Hetaryl substituted homotetramic and homotetronic acids and their use thereof as pesticides

ABSTRACT

The present invention relates to new hetaryl-substituted homotetramic and homotetronic acids of the formula (I)                  
 
in which
         A, B, Q 1 , Q 2 , W, G and Het have the meanings stated in the disclosure,   to a plurality of processes for their preparation, and to their use as pesticides, microbicides, and herbicides.

The present invention relates to new hetaryl-substituted homotetramicand homotetronic acids, to a plurality of processes for theirpreaparation, and to their use as pesticides, microbicides andherbicides.

It is known that certain tetrahydropyridones have herbicidal properties:JP-A-08-325230. Moreover, there are known specific4-hydroxytetrahydropyridones which have acaricidal, insecticidal andherbicidal properties: JP-A-11 152 273.

However, the activity and range of action of these compounds is notalways entirely satisfactory, in particular when low application ratesand concentrations are used. Furthermore, these compounds are not alwayssufficiently well tolerated by plants.

It is furthermore known that certain 5,6-dihydropyrone derivatives, asprotease inhibitors, have antiviral properties: WO 95/14012.Furthermore, 4-phenyl-6-(2-phenethyl)-5,6-dihydropyrone is known fromthe synthesis of kawalactone derivatives: Kappe et al.; Arch. Pharm.309, 558–64, (1976). Moreover, 5,6-dihydropyrone derivatives are knownas intermediates: White, J. D., Brenner, J. B., Deinsdale, M. J., J.Amer. Chem. Soc. 93, 281–2 (1971). Applications in crop protection havenot been described as yet.

There have now been found new compounds of the formula (I)

in which

-   Het represents a nitrogen-containing 5-membered heterocyclic ring    which is substituted by halogen, alkyl, alkoxy, alkenyloxy,    halogenoalkyl, halogenoalkoxy, halogenoalkenyloxy, cyano, nitro,    alkylthio, alkylsulphinyl, alkylsulphonyl, optionally substituted    phenyl or optionally substituted phenoxy,-   W represents oxygen or N-D,-   A represents hydrogen, in each case optionally halogen-substituted    alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl,    saturated or unsaturated, optionally substituted cycloalkyl in which    at least one ring atom is optionally replaced by a hetero atom, or    represents aryl, arylalkyl or hetaryl, each of which is optionally    substituted by halogen, alkyl, halogenoalkyl, alkoxy,    halogenoalkoxy, cyano or nitro,-   B represents hydrogen or alkyl, or-   A and B together with the carbon atom to which they are bonded    represent a saturated or unsaturated, unsubstituted or substituted    cycle which optionally contains at least one hetero atom;-   D represents hydrogen or an optionally substituted radical from the    series comprising alkyl, alkenyl, alkinyl, alkoxyalkyl,    polyalkoxyalkyl, alkylthioalkyl, saturated or unsaturated cycloalkyl    in which one or more ring members are optionally replaced by hetero    atoms, or arylalkyl, aryl, hetarylalkyl or hetaryl, or-   A and Q¹ together represent alkanediyl which is optionally    substituted by in each case optionally substituted alkyl or alkoxy    and in which two carbon atoms which are not directly adjacent    optionally form a further optionally substituted cycle, or-   D and Q¹ together with the atoms to which they are bonded represent    a saturated or unsaturated cycle which optionally contains at least    one hetero atom and which is unsubstituted or substituted in the D,    Q¹ moiety,-   Q¹ represents hydrogen, alkyl, alkoxyalkyl, optionally substituted    cycloalkyl (in which one methylene group is optionally replaced by    oxygen or sulphur) or optionally substituted phenyl,-   Q² represents hydrogen or alkyl, or-   Q¹ and Q² together with the carbon atom to which they are bonded    represent an unsubstituted or substituted cycle which optionally    contains one hetero atom,-   G represents hydrogen (a) or one of the groups

-    in which-   E represents a metal ion or an ammonium ion,-   L represents oxygen or sulphur,-   M represents oxygen or sulphur,-   R¹ represents in each case optionally halogen-substituted alkyl,    alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or represents    cycloalkyl which is optionally substituted by halogen, alkyl or    alkoxy and which can be interrupted by at least one hetero atom, in    each case optionally substituted phenyl, phenylalkyl, hetaryl,    phenoxyalkyl or hetaryloxyalkyl,-   R² represents in each case optionally halogen-substituted alkyl,    alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally    substituted cycloalkyl, phenyl or benzyl,-   R³ represents optionally alkyl, halogenoalkyl or optionally    substituted phenyl or benzyl,-   R⁴ and R⁵ independently of one another represent in each case    optionally halogen-substituted alkyl, alkoxy, alkylamino,    dialkylamino, alkylthio, alkenylthio, cycloalkylthio and in each    case optionally substituted phenyl, benzyl, phenoxy or phenylthio,-   R⁶ and R⁷ independently of one another represent hydrogen, in each    case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,    alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally    substituted benzyl, or together with the N atom to which they are    bonded represent a cycle which is optionally interrupted by oxygen    or sulphur.

Depending on the nature of the substituents, the compounds of theformula (I) can exist as geometric and/or optical isomers or isomermixtures of various compositions, and, if appropriate, these can beseparated in the customary fashion. Not only the pure isomers, but alsothe isomer mixtures, their preparation and use and compositionscomprising them are subject-matter of the present invention. However,the following text will, for the sake of simplicity, always mentioncompounds of the formula (I), even though this is understood as meaningnot only the pure compounds, but also, if appropriate, mixtures withvarious amounts of isomeric compounds.

Depending on the position of the substituent G, the compounds of theformula (I) can exist in the two isomeric forms of the formulae (I-A)and (I-B),

which is expressed by the broken line in formula (I).

The compounds of the formulae (I-A) and (I-B) can exist not only asmixtures, but also in the form of their pure isomers. If appropriate,mixtures of the compounds of the formulae (I-A) and (I-B) can beseparated in a manner known per se by physical methods, for example bychromatographic methods.

The following text will only mention in each case one of the isomerswhich are possible, for the sake of clarity. This does not exclude that,if appropriate, the compounds may exist in the form of the isomermixtures or in each case in the other isomeric form.

Taking into consideration the meanings thiazolyl for Het and oxygen andN-D for W, the following main structures (I-1) and (I-2) result

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-1-a) to (I-1-g)result if W is N-D (1),

in which

A, B, D, E, L, M, Q¹, Q², R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have theabovementioned meanings,

X represents hydrogen, halogen, alkyl, alkoxy, alkenyloxy, nitro, cyanoor optionally substituted phenyl and

Y represents halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, orin each case optionally substituted phenyl or phenoxy.

Taking into consideration the various meanings (a), (b), (c), (d), (e),(f) and (g) of group G, the following main structures (I-2-a) to (I-2-g)result if W is oxygen (2),

where

A, B, E, L, M, Q¹, Q², X, Y, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have theabovementioned meanings.

Furthermore, it has been found that the new compounds of the formula (I)are obtained by one of the processes described hereinbelow:

-   (A) Substituted tetrahydropyridine-2,4-diones or their enols of the    formula (I-1-a)

-   -   in which    -   A, B, D, Q¹, Q² and Het have the abovementioned meanings are        obtained when    -   N-acylamino acid esters of the formula (II)

-   -   in which    -   A, B, D, Q¹, Q² and Het have the abovementioned meanings and    -   R⁸ represents alkyl (preferably C₁–C₆-alkyl)    -   are subjected to an intramolecular condensation reaction in the        presence of a diluent and in the presence of a base.

Furthermore, it has been found

-   (B) that substituted 5,6-dihydropyrones of the formula (I-2-a)

-   -   in which    -   A, B, Q¹, Q² and Het have the abovementioned meanings are        obtained when    -   O-acylhydroxycarboxylic esters of the formula (III)

-   -   in which    -   A, B, Q¹, Q² and Het have the abovementioned meanings,    -   and    -   R⁸ represents alkyl (preferably C₁–C₆-alkyl)    -   are subjected to an intramolecular condensation reaction in the        presence of a diluent and in the presence of a base.

Furthermore, it has been found,

-   (C) that the compounds of the formulae (I-1-b) to (I-2-b) shown    above in which A, B, Q¹, Q², R¹, W and Het have the abovementioned    meanings are obtained when compounds of the formulae (I-1-a) to    (I-2-a) shown above in which A, B, Q¹, Q², W and Het have the    abovementioned meanings are reacted in each case-   (α) with acid halides of the formula (IV)

-   -   in which    -   R¹ has the abovementioned meaning and    -   Hal represents halogen (in particular chlorine or bromine) or

-   (β) with carboxylic anhydrides of the formula (V)    R¹—CO—O—CO—R¹  (V)    -   in which    -   R¹ has the abovementioned meaning,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (D) that the compounds of the formulae (I-1-c) to (I-2-c) shown    above in which A, B, Q¹, Q², R², M, W and Het have the    abovementioned meanings and L represents oxygen are obtained when    compounds of the formulae (I-1-a) to (I-2-a) shown above in which A,    B, Q¹, Q², W and Het have the abovementioned meanings are reacted in    each case    -   with chloroformic esters or chloroformic thioesters of the        formula (VI)        R²-M-CO—Cl  (VI)    -   in which    -   R² and M have the abovementioned meaning,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (E) that the compounds of the formulae (I-1-c) to (I-2-c) shown    above in which A, B, Q¹, Q², R², M, W and Het have the    abovementioned meanings and L represents sulphur are obtained when    compounds of the formulae (I-1-a) to (I-2-a) shown above in which A,    B, Q¹, Q², W and Het have the abovementioned meanings are reacted in    each case    -   with chloromonothioformic esters or chlorodithioformic esters of        the formula (VII)

-   -   in which    -   M and R² have the abovementioned meanings,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,    -   and

-   (F) that compounds of the formulae (I-1-d) to (I-2-d) shown above in    which A, B, Q¹, Q², R³, W and Het have the abovementioned meanings    are obtained when compounds of the formulae (I-1-a) and (I-2-a)    shown above in which A, B, Q¹, Q², W and Het have the abovementioned    meanings are reacted in each case    -   with sulphonyl chlorides of the formula (VIII)        R³—SO₂—Cl  (VIII)    -   in which:    -   R³ has the abovementioned meaning,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (G) that compounds of the formulae (I-1-e) to (I-2-e) shown above in    which A, B, L, Q¹, Q², R⁴, R⁵, W and Het have the abovementioned    meanings are obtained when compounds of the formulae (I-1-a) to    (I-2-a) shown above in which A, B, Q¹, Q², W and Het have the    abovementioned meanings are reacted in each case    -   with phosphorus compounds of the formula (IX)

-   -   in which    -   L, R⁴ and R⁵ have the abovementioned meanings and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (H) that compounds of the formulae (I-1-f) to (I-2-f) shown above in    which A, B, E, Q¹, Q², W and Het have the abovementioned meanings    are obtained when compounds of the formulae (I-1-a) to (I-2-a) in    which A, B, Q¹, Q², W and Het have the abovementioned meanings are    reacted in each case    -   with metal compounds or amines of the formula (X) or (XI)

-   -   in which    -   Me represents a monovalent or divalent metal (preferably an        alkali metal or alkaline earth metal such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R¹¹, R¹², R¹³ independently of one another represent hydrogen or        alkyl (preferably C₁–C₈-alkyl)    -   are reacted, if appropriate in the presence of a diluent,

-   (I) that compounds of the formulae (I-1-g) to (I-2-g) shown above in    which A, B, L, Q¹, Q², R⁶, R⁷, W and Het have the abovementioned    meanings are obtained when compounds of the formulae (I-1-a) to    (I-2-a) shown above in which A, B, Q¹, Q², W and Het have the    abovementioned meanings are reacted in each case

-   (α) with isocyanates or isothiocyanates of the formula (XII)    R⁶—N═N═C=L  (XII)    -   in which    -   R⁶ and L have the abovementioned meanings,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst, or

-   (β) with carbamoyl chlorides or thiocarbamoyl chlorides of the    formula (XIII)

-   -   in which    -   L, R⁶ and R⁷ have the abovementioned meanings,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of acid binder.

Furthermore, it has been found that the new compounds of the formula (I)have very good activity as pesticides, preferably as insecticides,acaricides and also herbicides.

Formula (I) provides a general definition of the compounds according tothe invention. Preferred substituents or ranges of the radicals statedin the formulae mentioned hereinabove and hereinbelow are illustrated inthe following text:

-   Het preferably represents

-   W preferably represents oxygen or N-D,-   X preferably represents hydrogen, halogen, C₁–C₆-alkyl,    C₁–C₆-alkoxy, C₃–C₆-alkenyloxy, nitro, cyano, or represents phenyl    which is optionally substituted by halogen, C₁–C₆-alkyl,    C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, nitro or    cyano,-   Y preferably represents halogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl,    C₁–C₆-alkoxy, C₁–C₆-halogenoalkoxy or the groups

-   V¹ preferably represents hydrogen, halogen, C₁–C₁₂-alkyl,    C₁–C₆-alkoxy, C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl,    C₁–C₆-alkylsulphonyl, C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy,    nitro, cyano, or represents phenyl, phenoxy, phenoxy-C₁–C₄-alkyl,    phenyl-C₁–C₄-alkoxy, phenylthio-C₁–C₄-alkyl or    phenyl-C₁–C₄-alkylthio, each of which is optionally monosubstituted    or polysubstituted by halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, nitro or cyano,-   V² and V³ preferably independently of one another represent    hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl or    C₁–C₄-halogenoalkoxy,-   V¹ and V² together with the carbon atoms to which they are bonded    preferably represent a 5- or 6-membered cycle which is optionally    substituted by C₁–C₄-alkyl or halogen and in which one to three    carbon atoms can optionally be replaced by oxygen, sulphur or    nitrogen,-   A preferably represents hydrogen, or represents C₁–C₁₂-alkyl,    C₃–C₈-alkenyl, C₁–C₆-alkoxy-C₁–C₄-alkyl, each of which is optionally    substituted by halogen, or represents optionally halogen-,    C₁–C₄-alkyl- or C₁–C₄-alkoxy-substituted C₃–C₈-cycloalkyl or    C₃–C₆-cycloalkyl-C₁–C₄-alkyl in which one or two ring members which    are not directly adjacent are optionally replaced by oxygen and/or    sulphur, or represents phenyl, benzyl, hetaryl having 5 to 6 ring    atoms (for example furanyl, pyridyl, imidazolyl, triazolyl,    pyrazolyl, pyrimidyl, thiazolyl or thienyl) or hetaryl-C₁–C₄-alkyl    having 5 to 6 ring atoms (for example pyridyl, pyrimidyl or    thiazolyl), each of these cycles optionally being substituted by    halogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy,    C₁–C₆-halogenoalkoxy, cyano or nitro,-   B preferably represents hydrogen or C₁–C₆-alkyl,-   A, B and the carbon atom to which they are bonded preferably    represent saturated C₃–C₁₀-cycloalkyl or unsaturated    C₅–C₁₀-cycloalkyl in which one ring member is optionally replaced by    oxygen or sulphur and which are optionally monosubstituted or    disubstituted by C₁–C₆-alkyl, C₃–C₈-cycloalkyl, C₁–C₆-halogenoalkyl,    C₁–C₆-alkoxy, C₁–C₆-alkylthio, halogen or phenyl,-   D preferably represents hydrogen, in each case optionally    halogen-substituted C₁–C₆-alkyl, C₃–C₈-alkenyl, C₃–C₈-alkinyl,    C₁–C₆-alkoxy-C₂–C₆-alkyl, or represents optionally halogen-,    C₁–C₄-alkyl-, C₁–C₄-alkoxy- or C₁–C₄-halo-genoalkyl-substituted    C₃–C₈-cycloalkyl or C₃–C₆-cycloalkyl-C₁–C₄-alkyl in which one ring    member is optionally replaced by oxygen or sulphur,-   A and Q¹ jointly preferably represent C₃–C₆-alkanediyl which is    optionally substituted by C₁–C₄-alkyl or C₁–C₄-alkoxy,-   D and Q¹ together preferably represent C₃–C₆-alkanediyl which is    optionally monosubstituted or disubstituted by identical or    different substituents from the series consisting of C₁–C₄-alkyl and    C₁–C₄-alkoxy, or-   Q¹ preferably represents hydrogen, C₁–C₆-alkyl,    C₁–C₆-alkoxy-C₁–C₂-alkyl, or represents C₃–C₈-cycloalkyl in which    one methylene group is optionally replaced by oxygen or sulphur and    which is optionally substituted by fluorine, chlorine, C₁–C₄-alkyl,    C₁–C₂-halogenoalkyl or C₁–C₄-alkoxy, or represents phenyl which is    optionally substituted by halogen, C₁–C₄-alkyl, C₁–C₄-alkoxy,    C₁–C₂-halogenoalkyl, C₁–C₂-halogenoalkoxy, cyano or nitro, or-   Q² preferably represents hydrogen or C₁–C₄-alkyl,-   Q¹ and Q² preferably together with the carbon atom to which they are    bonded represent C₃–C₇-cycloalkyl in which one ring member is    optionally replaced by oxygen or sulphur and which is optionally    substituted by C₁–C₆-alkyl, C₁–C₆-alkoxy or C₁–C₂-halogenoalkyl,-   G preferably represents hydrogen (a) or one of the groups

-   -   E (f) or

-   -    (g), in particular (a), (b), (c) or (g),    -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ preferably represents C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl,    C₁–C₈-alkoxy-C_(1–C) ₈-alkyl, C₁–C₈-alkylthio-C₁–C₈-alkyl,    poly-C₁–C₈-alkoxy-C₁–C₈-alkyl, each of which is optionally    substituted by halogen, or represents C₃–C₈-cycloalkyl in which one    or more (preferably one or two) ring members which are not directly    adjacent are optionally replaced by oxygen and/or sulphur and which    is optionally substituted by halogen, C₁–C₆-alkyl or C₁–C₆-alkoxy,    -   or represents phenyl which is optionally substituted by halogen,        cyano, nitro, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₆-halogenoalkyl,        C₁–C₆-halogenoalkoxy, C₁–C₆-alkylthio or C₁–C₆-alkylsulphonyl,    -   or represents phenyl-C₁–C₆-alkyl which is optionally substituted        by halogen, nitro, cyano, C₁–C₆-alkyl, C₁–C₆-alkoxy,        C₁–C₆-halogenoalkyl or C₁–C₆-halogenoalkoxy,    -   or represents 5- or 6-membered hetaryl (for example pyrazolyl,        thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl) which is        optionally substituted by halogen, C₁–C₆-alkyl or        trifluoromethyl,    -   or represents phenoxy-C₁–C₆-alkyl which is optionally        substituted by halogen or C₁–C₆-alkyl,    -   or represents 5- or 6-membered hetaryloxy-C₁–C₆-alkyl (for        example pyridyloxy-C₁–C₆-alkyl, pyrimidyloxy-C₁–C₆-alkyl or        thiazolyloxy-C₁–C₆-alkyl), which is optionally substituted by        halogen, amino or C₁–C₆-alkyl,

-   R² preferably represents C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl,    C₁–C₈-alkoxy-C₂–C₈-alkyl, poly-C₁–C₈-alkoxy-C₂–C₈-alkyl, each of    which is optionally substituted by halogen,    -   or represents C₃–C₈-cycloalkyl which is optionally substituted        by halogen, C₁–C₆-alkyl or C₁–C₆-alkoxy,    -   or represents phenyl or benzyl, each of which is optionally        substituted by halogen, cyano, nitro, C₁–C₆-alkyl, C₁–C₆-alkoxy,        C₁–C₆-halogenoalkyl or C₁–C₆-halogenalkoxy,

-   R³ preferably represents C₁–C₈-alkyl which is optionally substituted    by halogen or represents phenyl or benzyl, each of which is    optionally substituted by halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, cyano or nitro,

-   R⁴ and R⁵ preferably independently of one another represent    C₁–C₈-alkyl, C₁–C₈-alkoxy, C₁–C₈-alkylamino, di-(C₁–C₈-alkyl)amino,    C₁–C₈-alkylthio, C₂–C₈-alkenylthio, C₃–C₇-cycloalkylthio, each of    which is optionally substituted by halogen, or represent phenyl,    benzyl, phenoxy or phenylthio, each of which is optionally    substituted by halogen, nitro, cyano, C₁–C₄-alkoxy,    C₁–C₄-halogenoalkoxy, C₁–C₄-alkylthio, C₁–C₄-halogenoalkylthio,    C₁–C₄-alkyl or C₁–C₄-halogenoalkyl,

-   R⁶ and R⁷ independently of one another preferably represent    hydrogen, or represent C₁–C₈-alkyl, C₃–C₈-cycloalkyl, C₁–C₈-alkoxy,    C₃–C₈-alkenyl, C₁–C₈-alkoxy-C₁–C₈-alkyl, each of which is optionally    substituted by halogen, or represent phenyl which is optionally    substituted by halogen, C₁–C₈-halogenoalkyl, C₁–C₈-alkyl or    C₁–C₈-alkoxy, or represent benzyl which is optionally substituted by    halogen, C₁–C₈-alkyl, C₁–C₈-halogenoalkyl or C₁–C₈-alkoxy, or    together with the N atom to which they are bonded represent a    C₃–C₆-alkylene radical in which one carbon atom is optionally    replaced by oxygen or sulphur and which is optionally substituted by    C₁–C₄-alkyl.

In the definitions of radicals mentioned as being preferred, halogen,also as a substituent such as, for example, in halogenoalkyl, representsfluorine, chlorine, bromine and iodine, in particular fluorine orchlorine.

-   Het especially preferably represents

-   W especially preferably represents oxygen or N-D,-   X especially preferably represents hydrogen, chlorine, bromine,    C₁–C₄-alkyl, or represents phenyl which is optionally    monosubstituted to disubstituted by fluorine, chlorine, bromine,    C₁–C₄-alkyl, C₁–C₂-halogenoalkoxy, nitro or cyano,-   Y especially preferably represents chlorine, bromine, C₁–C₄-alkyl,    C₁–C₄-halogenoalkyl, C₁–C₄-alkoxy, C₁–C₄-halogenoalkoxy or the    groups

-   V¹ especially preferably represents hydrogen, fluorine, chlorine,    bromine, C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl,    C₁–C₂-halogenalkoxy, nitro, cyano, or represents phenyl, phenoxy,    phenoxy-C₁–C₂-alkyl, phenyl-C₁–C₂-alkoxy, phenylthio-C₁–C₂-alkyl or    phenyl-C₁–C₂-alkylthio, each of which is optionally monosubstituted    or disubstituted by fluorine, chlorine, bromine, C₁–C₄-alkyl,    C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl, C₁–C₂-halogenoalkoxy, nitro or    cyano-   V² especially preferably represents hydrogen, fluorine, chlorine,    bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl or    C₁–C₂-halogenoalkoxy,-   V¹ and V² jointly together with the carbon atoms to which they are    bonded especially preferably represent a 5- or 6-membered cycle in    which one or two carbon atoms can optionally be replaced by oxygen    and which is optionally substituted by fluorine or methyl,-   A especially preferably represents hydrogen, or represents    C₁–C₈-alkyl or C₁–C₄-alkoxy-C₁–C₂-alkyl, each of which is optionally    substituted by fluorine, or represents C₅–C₆-cycloalkyl or    C₃–C₆-cycloalkyl-C₁–C₂-alkyl in which one ring member is optionally    replaced by oxygen or sulphur and which is optionally substituted by    fluorine, chlorine, methyl, ethyl or methoxy, or represents phenyl    or benzyl, each of which is optionally substituted by fluorine,    chlorine, bromine, C₁–C₄-alkyl, C₁–C₂-halogenoalkyl, C₁–C₄-alkoxy or    C₁–C₂-halogenoalkoxy,-   B especially preferably represents hydrogen or C₁–C₄-alkyl,-   A, B and the carbon atom to which they are bonded especially    preferably represent saturated C₅–C₇-cycloalkyl in which one ring    member is optionally replaced by oxygen and which is optionally    monosubstituted by C₁–C₄-alkyl, trifluoromethyl or C₁–C₄-alkoxy,-   D especially preferably represents hydrogen, or represents    C₁–C₆-alkyl, C₃–C₆-alkenyl or C₁–C₄-alkoxy-C₂–C₃-alkyl, each of    which is optionally substituted by fluorine, or represents    C₃–C₇-cycloalkyl or C₃–C₆-cycloalkyl-C₁–C₂-alkyl in which one    methylene group is optionally replaced by oxygen and which is    optionally substituted by C₁–C₂-alkyl, fluorine or chlorine,-   A and Q¹ jointly especially preferably represent C₃–C₄-alkanediyl,-   D and Q¹ jointly especially preferably represent C₃–C₄-alkanediyl,-   Q¹ especially preferably represents hydrogen, C₁–C₄-alkyl,    C₁–C₄-alkoxy-C₁–C₂-alkyl, or represents C₃–C₆-cycloalkyl in which    one methylene group is optionally replaced by oxygen and which is    optionally substituted by methyl or methoxy,-   Q² especially preferably represents hydrogen, methyl or ethyl,-   Q¹ and Q² especially preferably jointly with the carbon atom to    which they are bonded represent saturated C₅–C₆-cycloalkyl in which    one ring member is optionally replaced by oxygen and which is    optionally substituted by C₁–C₄-alkyl or C₁–C₄-alkoxy,-   G especially preferably represents hydrogen (a) or one of the groups

-   -   E (f) or

-   -    (g), in particular (a), (b), (c) or (g),    -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,

-   R¹ especially preferably represents C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl,    C₁–C₄-alkoxy-C₁–C₂-alkyl, C₁–C₄-alkylthio-C₁–C₂-alkyl, each of which    is optionally substituted by fluorine or chlorine, or represents    C₃–C₇-cycloalkyl in which one or two ring members which are not    directly adjacent are optionally replaced by oxygen and/or sulphur    and which is optionally substituted by fluorine, chlorine,    C₁–C₅-alkyl or C₁–C₅-alkoxy,    -   or represents phenyl which is optionally substituted by        fluorine, chlorine, bromine, cyano, nitro, C₁–C₄-alkyl,        C₁–C₄-alkoxy, trifluoromethyl or trifluoromethoxy;    -   or represents pyridyl or thienyl, each of which is optionally        substituted by fluorine, chlorine, bromine, methyl, ethyl or        trifluoromethyl,

-   R² especially preferably represents C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl or    C₁–C₄-alkoxy-C₂–C₄-alkyl, each of which is optionally substituted by    fluorine,    -   or represents C₃–C₇-cycloalkyl which is optionally, substituted        by methyl, ethyl or methoxy,    -   or represents phenyl or benzyl, each of which is optionally        substituted by fluorine, chlorine, bromine, cyano, nitro,        C₁–C₄-alkyl, C₁–C₃-alkoxy, trifluoromethyl or trifluoromethoxy,

-   R³ especially preferably represents C₁–C₆-alkyl which is optionally    substituted by fluorine, or represents phenyl which is substituted    by fluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy,    trifluoromethyl, trifluoromethoxy, cyano or nitro,

-   R⁴ especially preferably represents C₁–C₆-alkyl, C₁–C₆-alkoxy,    C₁–C₆-alkyl amino, di-(C₁–C₆-alkyl)amino, C₁–C₆-alkylthio, or    represents phenyl, benzyl, phenoxy or phenylthio, each of which is    optionally substituted by fluorine, chlorine, bromine, nitro, cyano,    C₁–C₃-alkoxy, trifluoromethoxy, C₁–C₃-alkyl or trifluoromethyl,

-   R⁵ especially preferably represents C₁–C₄-alkyl, C₁–C₄-alkoxy or    C₁–C₄-alkylthio,

-   R⁶ especially preferably represents hydrogen, C₁–C₆-alkyl,    C₃–C₆-cycloalkyl, C₁–C₆-alkoxy, C₃–C₆-alkenyl,    C₁–C₆-alkoxy-C₁–C₆-alkyl, or represents phenyl which is optionally    substituted by fluorine, chlorine, bromine, trifluoromethyl,    C₁–C₄-alkyl or C₁–C₄-alkoxy, or represents benzyl which is    optionally substituted by fluorine, chlorine, bromine, methyl,    ethyl, trifluoromethyl or methoxy,

-   R⁷ especially preferably represents hydrogen, C₁–C₆-alkyl or    C₃–C₆-alkenyl,

-   R⁶ and R⁷ especially preferably together with the N atom to which    they are bonded represent a C₄–C₆-alkylene radical in which one    methylene group is optionally replaced by oxygen or sulphur and    which is optionally substituted by methyl or ethyl.

In the definitions of radicals which have been mentioned as beingespecially preferred, halogen, also as substituent such as, for example,in halogenoalkyl, represents fluorine, chlorine, bromine and iodine,especially fluorine and chlorine, very especially fluorine.

-   Het very especially preferably represents

-   W very especially preferably represents oxygen or N-D,-   X very especially preferably represents chlorine, bromine, methyl,    ethyl, n-propyl, isopropyl, n-butyl or isobutyl,-   Y very especially preferably represents methyl, ethyl, n-propyl,    isopropyl, n-butyl, isobutyl, tert-butyl or the group

-   V¹ very especially preferably represents hydrogen, fluorine,    chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy,    trifluoromethyl, trifluoromethoxy,-   V² very especially preferably represents hydrogen, fluorine,    chlorine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy,    trifluoromethyl or trifluoromethoxy,-   A very especially preferably represents hydrogen, methyl, ethyl,    propyl, isopropyl, butyl, isobutyl, methoxymethyl, ethoxymethyl,-   B very especially preferably represents hydrogen, methyl or ethyl,-   A, B and the carbon atom to which they are bonded very especially    preferably represent saturated C₅–C₆-cycloalkyl in which one ring    member is optionally replaced by oxygen and which is optionally    monosubstituted by methyl, ethyl, n-propyl, isopropyl, butyl,    trifluoromethyl, methoxy, ethoxy, n-propoxy or n-butoxy,-   D very especially preferably represents hydrogen, methyl, ethyl,    propyl, isopropyl, allyl, 2-butenyl, methoxyethyl, ethoxyethyl,    cyclopropyl, cyclopentyl or cyclohexyl,-   A and Q¹ jointly very especially preferably represent    C₃–C₄-alkanediyl.-   D and Q¹ jointly very especially preferably represent    C₃–C₄-alkanediyl,-   Q¹ very especially preferably represents hydrogen, methyl, ethyl,    propyl, isopropyl, cyclopropyl, cyclopentyl or cyclohexyl,-   Q² very especially preferably represents hydrogen, methyl or ethyl,-   Q¹ and Q² very especially preferably jointly with the carbon to    which they are bonded represent saturated C₅–C₆-cycloalkyl in which    one ring member is optionally replaced by oxygen and which is    optionally substituted by methyl, ethyl, propyl, isopropyl, methoxy,    ethoxy, propoxy or butoxy,-   G very especially preferably represents hydrogen (a) or one of the    groups

-   E (f) or

-    (g), in particular (a), (b), (c) or (g),    -   in which    -   E represents a metal ion or an ammonium ion,    -   L represents oxygen or sulphur and    -   M represents oxygen or sulphur,-   R¹ very especially preferably represents C₁–C₄-alkyl,    C₂–C₁₄-alkenyl, C₁–C₄-alkoxy-C₁–C₂-alkyl,    C₁–C₄-alkylthio-C₁–C₂-alkyl, each of which is optionally substituted    by fluorine or chlorine, or represents C₃–C₆-cycloalkyl in which one    or two ring members which are not directly adjacent are optionally    replaced by oxygen and/or sulphur and which is optionally    substituted by fluorine, chlorine, methyl, ethyl or methoxy,    -   or represents phenyl which is optionally substituted by        fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl,        isopropyl, tert-butyl, methoxy, trifluoromethyl or        trifluoromethoxy,    -   or represents thienyl or pyridyl, each of which is optionally        substituted by fluorine, chlorine, bromine or methyl,-   R² very especially preferably represents C₁–C₁₄-alkyl,    C₂–C₁₄-alkenyl or C₁–C₄-alkoxy-C₂–C₃-alkyl, each of which is    optionally substituted by fluorine,    -   or represents C₃–C₆-cycloalkyl which is optionally substituted        by methyl, ethyl or methoxy,    -   or represents phenyl or benzyl, each of which is optionally        substituted by fluorine, chlorine, cyano, nitro, methyl, ethyl,        isopropyl, tert-butyl, methoxy, trifluoromethyl or        trifluoromethoxy,-   R³ very especially preferably represents methyl, ethyl, n-propyl,    isopropyl, each of which is optionally substituted by fluorine, or    represents phenyl which is optionally substituted by fluorine,    chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl,    trifluoromethoxy, cyano or nitro,-   R⁴ very especially preferably represents C₁–C₄-alkyl, C₁–C₄-alkoxy,    C₁–C₄-alkylamino, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylthio or    represents phenyl, phenoxy or phenylthio, each of which is    optionally substituted by fluorine, chlorine, bromine, nitro, cyano,    C₁–C₂-alkoxy, trifluoromethoxy or C₁–C₃-alkyl,-   R⁵ very especially preferably represents methyl, ethyl, methoxy,    ethoxy, methylthio or ethylthio,-   R⁶ and R⁷ independently of one another very especially preferably    represent hydrogen, C₁–C₄-alkyl, C₃–C₆-cycloalkyl, C₁–C₄-alkoxy,    C₃–C₄-alkenyl, C₁–C₄-alkoxy-C₁–C₄-alkyl,-   R⁷ very especially preferably represents hydrogen, C₁–C₄-alkyl or    C₃–C₄-alkenyl,-   R⁶ and R⁷ very especially preferably together with the N atom to    which they are bonded represent a C₅–C₆-alkylene radical in which    one methylene group is optionally replaced by oxygen or sulphur.-   Het most especially preferably represents

-   W most especially preferably represents oxygen or N-D,-   X most especially preferably represents chlorine, methyl, ethyl,    n-propyl or i-propyl,-   Y most especially preferably represents

-   A most especially preferably represents hydrogen or methyl,-   B most especially preferably represents hydrogen or methyl,-   A, B and the carbon atom to which they are bonded most especially    preferably represent saturated C₆-cycloalkyl in which one ring    member is optionally replaced by oxygen,-   D most especially preferably represents hydrogen or cyclopropyl,-   D and Q¹ most especially preferably jointly represent    C₃–C₄-alkanediyl,-   Q¹ most especially preferably represents methyl or hydrogen,-   Q² most especially preferably represents methyl or hydrogen,-   Q¹ and Q² most especially preferably jointly with the carbon to    which they are bonded represent saturated C₆-cycloalkyl in which one    ring member is optionally replaced by oxygen,-   G most especially preferably represents hydrogen (a) or one of the    groups

-    where M represents oxygen or sulphur,-   R¹ most especially preferably represents C₁–C₄-alkyl,    C₁–C₄-alkoxy-C₁–C₂-alkyl, or represents phenyl or pyridyl, each of    which is optionally substituted by chlorine,-   R² most especially preferably represents C₁–C₄-alkyl, phenyl or    benzyl,-   R⁶ and R⁷ most especially preferably together with the N atom to    which they are bonded represent a C₅–C₆-alkylene radical in which    one methylene group is optionally replaced by oxygen.

The definitions or explanations stated above in general or in preferredranges can be combined with each other as desired, that is to saycombinations between the respective ranges and preferred ranges are alsopossible. They apply to the end products and, analogously, to theprecursors and intermediates.

Preferred in accordance with the invention are the compounds of theformula (I) with a combination of the meanings stated above as beingpreferred (given preference to).

Especially preferred in accordance with the invention are the compoundsof the formula (I) with a combination of the meanings stated above asespecially preferred.

Very especially preferred in accordance with the invention are thecompounds of the formula (I) with a combination of the meanings statedabove as very especially preferred.

Most especially preferred in accordance with the invention are thecompounds of the formula (I) with a combination of the meanings statedabove as most preferred.

Particularly preferred are compounds of the formula (I) in which G ishydrogen.

Further compounds of the formula (I) which are particularly preferredare those in which D represents hydrogen, methyl, ethyl, propyl,isopropyl, cyclopropyl, cyclopentyl or cyclohexyl.

Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl,also in connection with hetero atoms such as, for example, in alkoxy,can be in each case straight-chain or branched as far as this ispossible.

Unless otherwise defined, optionally substituted radicals can bemonosubstituted or polysubstituted, it being possible for thesubstituents to be identical or different in the case ofpolysubstitutions.

If, in accordance with process (A), ethylN-[4-(5-methyl)-2-(4-chlorophenyl)-thiazolylacetyl]-1-aminomethyl-cyclohexane-carboxylateis used as starting material, the course of the process according to theinvention can be represented by the following equation:

If, in accordance with process (B), ethylO-[4-(5-methyl)-2-(4-chlorophenyl)-thiazolylacetyl]-1-hydroxymethyl-cyclohexane-carboxylateis used as starting material, the course of the process according to theinvention can be represented by the following equation:

If, in accordance with process (Dα),3-[4-(5-methyl-2-(3-chlorophenyl)-thiazolyl]-4-hydroxy-6,6-dimethyldihydropyridin-2-oneand pivaloyl chloride are used as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

If, in accordance with process (Dβ),3-[4-(5-ethyl-2-(4-methoxyphenyl))-thiazolyl]-4-hydroxy-6,6-dimethyldihydropyroneand acetic anhydride are used as starting materials, the course of theprocess according to the invention can be represented by the followingequation:

If, in accordance with process (E),3-[4-(5-methyl-2-phenyl)-thiazolyl]-6,6-dimethyldihydropyridine-2,4-dioneand ethoxyethyl chloroformate are used as starting compounds, the courseof the process according to the invention can be represented by thefollowing equation:

If, in accordance with process (F),3-[4-(5-methyl-2-(4-fluorophenyl))-thiazolyl]-5,5,6,6-tetramethyldihydropyroneand methyl chloromonothioformate are used as starting materials, thecourse of the reaction can be represented as follows:

If, in accordance with process (G),3-[4-(5-methyl-3-(4-methylphenyl)-thiazolyl]-6,6-dimethyldihydropyridine-2,4-dioneand methanesulphonyl chloride are used as starting materials, the courseof the reaction can be represented by the following equation:

If, in accordance with process (H),3-[4-(5-methyl-2-phenyl)-thiazolyl]-4-hydroxy-5,5,6,6-tetramethyldihydropyroneand methanethio-phosphonyl chloride 2,2,2-trifluoroethyl ester are usedas starting materials, the course of the reaction can be represented bythe following equation:

If, in accordance with process (I,)3-[4-(5-methyl-2-(4-trifluoromethylphenyl))-thiazolyl]-6,6-dimethyl-dihydropyridine-2,4-dioneand NaOH are used as reactants, the course of the process according tothe invention can be represented by the following equation:

If, in accordance with process (Jα),3-[4-(5-methyl-2-(3-trifluoromethylphenyl))-thiazolyl]-4-hydroxy-5,5,6,6-tetramethyldihydropyroneand ethyl isocyanate are used as starting materials, the course of thereaction can be represented by the following equation:

If, in accordance with process (Jβ),3-[4-(5-methyl-2-phenyl)-thiazolyl]-6,6-dimethyl-dihydropyridine-2,4-dioneand dimethylcarbamoyl chloride are used as starting materials, thecourse of the reaction can be represented by the following scheme:

The compounds of the formula (II)

in which

A, B, D, Q¹, Q², Het and R⁸ have the abovementioned meanings and whichare required as starting materials in process (A) according to theinvention are new.

The acylamino acid esters of the formula (II) are obtained, for example,from amino acid derivatives of the formula (XIV)

in which

A, B, Q¹, Q², R⁸ and D have the abovementioned meanings are acylatedwith substituted hetaryl acetic acid derivatives of the formula (XV)

in which

-   Het has the abovementioned meaning and-   U represents a leaving group introduced by reagents for the    activation of carboxylic acids, such as carbonyldiimidazole,    carbonyldiimide (such as, for example, dicyclohexylcarbodiimide),    phosphorylating agents (such as, for example, POCl₃, BOP-Cl),    halogenating agents, for example thionyl chloride, oxalyl chloride,    phosgene or chloroformic ester-   (Chem. Reviews 52, 237–416 (1953); Bhattacharya, Indian J. Chem. 6,    341–5, 1968) or when acylamino acids of the formula (XVI)

in which

A, B, D, Q¹, Q² and Het have the abovementioned meanings are esterified(Chem. Ind. (London) 1568 (1968)).

The compounds of the formula (XVI)

in which

A, B, D, Q¹, Q² and Het have the abovementioned meanings are new.

The compounds of the formula (XVI) are obtained when β-amino acids ofthe formula (XVII)

in which

A, B, Q¹, Q² and D have the abovementioned meanings are acylated withsubstituted hetaryl acetic acid derivatives of the formula (XV)

in which

Het and U have the abovementioned meanings, for example following themethod of Schotten-Baumann (Organikum [Organic Chemistry], VEB DeutscherVerlag der Wissenschaften, Berlin 1977, p. 505).

Some of the compounds of the formula (XV) are new. They can besynthesized by methods known in principle (see, for example, H. Henecka,Houben-Weyl, Methoden der Organischen Chemie [Methods in OrganicChemistry], Vol. 8, pp. 467–469 (1952)) or they are prepared in situwith the abovementioned reagents.

The compounds of the formula (XV) are obtained, for example, by reactingsubstituted hetaryl acetic acids of the formula (XVIII)

in which

Het has the abovementioned meaning with halogenating agents (for examplethionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorustrichloride, phosphorus tribromide or phosphorus pentachloride), ifappropriate in the presence of a diluent (for example optionallychlorinated aliphatic or aromatic hydrocarbons such as toluene ormethylene chloride) at temperatures of from −20° C. to 150° C.,preferably from −10° C. to 100° C.

Some of the hetaryl acetic acids of the formula (XVIII) are commerciallyavailable, some of them are known or can be prepared by processes knownin principle (C. S. Rooney et al. J. Med. Chem. 26, 700–714 (1983);EP-A-368 592; M. S. Malamas et al. J. Med. Chem. 39, 237–246 (1996); J.L. Collins et al. J. Med. Chem. 41, 5037–5054 (1998); NL-A-66 14 130).

Some of the compounds of the formulae (XIV) and (XVII) are known and/orcan be synthesized by known methods (see, for example, T. Suzuki et al.,Synthetic Commun. 28, 701 (1998), R. Graf, Justus Liebigs Ann. Chem.661, 111 (1963)).

Furthermore, the starting materials of the formula (II)

in which

A, B, D, Q¹, Q², Het and R⁸ have the abovementioned meanings and whichare used in the above process (A) can be prepared when aminonitriles ofthe formula (XIX)

in which

A, B, Q¹, Q² and D have the abovementioned meanings are reacted withsubstituted hetaryl acetic acid derivatives of the formula (XV)

in which

Het and U have the abovementioned meanings to give compounds of theformula (XX)

in which

A, B, D, Q¹, Q² and Het have the abovementioned meanings andsubsequently subjecting the latter to acid alcoholysis.

The compounds of the formula (XX) are also new.

Some of the aminonitriles of the formula (XIX) are new and/or can beprepared by known processes (T. Suzuki et al., Chem. Pharm. Bull. 46,1116 (1998)).

The compounds of the formula (III)

in which

A, B, Q¹, Q², Het and R⁸ have the abovementioned meanings and which arerequired as starting materials in process (B) according to the inventionare new.

The acylhydroxycarboxylic esters of the formula (III) are obtained, forexample, when hydroxycarboxylic esters of the formula (XXI)

in which

A, B, Q¹, Q² and R⁸ have the abovementioned meanings are acylated withsubstituted hetaryl acetic acid derivatives of the formula (XV)

in which

Het and U have the abovementioned meaning (see preparation example ofcompounds of the formula (III)).

Some of the compounds of the formula (XXI) are known, commerciallyavailable or can be prepared by processes known in principle, forexample by Refornatskij Synthesis (Organikum, VEB Deutscher Verlag derWissenschaften, Berlin 1990, 18^(th) Ed., p. 501 et seq.)

The acid halides of the formula (IV), carboxylic anhydrides of theformula (V), chloroformic esters or chloroformic thioesters of theformula (VI), chloromonothioformic esters or chlorodithioformic estersof the formula (VII), sulphonyl chlorides of the formula (VIII),phosphorus compounds of the formula (IX) and metal hydroxides, metalalkoxides or amines of the formulae (X) and (XI) and isocyanates of theformula (XII) and carbamoyl chlorides of the formula (XIII), all ofwhich are furthermore required as starting materials for carrying outprocesses (C), (D), (E), (F), (G), (H) and (I) according to theinvention, are generally known compounds of organic or inorganicchemistry.

Some of the compounds of the formulae (XIV), (XVII), (XVIII), (XIX) and(XXI) are commercially available, some of them are known and/or can beprepared by methods known in principle.

Process (A) is characterized in that compounds of the formula (II) inwhich A, B, D, Q¹, Q², Het and R⁸ have the abovementioned meanings aresubjected to an intramolecular condensation reaction in the presence ofa base.

Diluents which can be employed in process (A) according to the inventionare all inert organic solvents. The following can preferably be used:hydrocarbons such as toluene and xylene, furthermore ethers such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide, dimethylacetamide andN-methyl-pyrrolidone, and also alcohols such as methanol, ethanol,propanol, isopropanol, butanol, isobutanol and tert-butanol.

Bases (deprotonating agents) which can be employed when carrying outprocess (A) according to the invention are all customary protonacceptors. The following can preferably be used: the oxides, hydroxidesand carbonates of alkali metals and alkaline earth metals, such assodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide,sodium carbonate, potassium carbonate and calcium carbonate, all ofwhich can also be employed in the presence of phase-transfer catalystssuch as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈–C₁₀)ammoniumchloride) or TDA 1 (=tris-(methoxyethoxyethyl)-amine). Alkali metalssuch as sodium or potassium can furthermore be used. Amides and hydridesof alkali metals and alkaline earth metals, such as sodium amide, sodiumhydride and calcium hydride are further possible materials which can beused, as are, moreover, alkali metal alkoxides such as sodium methoxide,sodium ethoxide and potassium tert-butoxide.

When carrying out process (A) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures of between −80° C. and 180° C.,preferably between −50° C. and 120° C.

Process (A) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (A) according to the invention, the reactantsof the formula (II) and the deprotonating bases are generally employedin approximately twice the equimolar amounts. However, it is possible touse one or the other reactants in a larger excess (up to 3 mol).

Process (B) is characterized in that compounds of the formula (III) inwhich A, B, Q¹, Q², Het and R⁸ have the abovementioned meanings aresubjected to an intramolecular condensation reaction in the presence ofa diluent and in the presence of a base.

Diluents which can be employed in process (B) according to the inventionare all inert organic solvents. The following can preferably be used:hydrocarbons such as toluene and xylene, furthermore ethers such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methyl-pyrrolidone, andalso alcohols such as methanol, ethanol, propanol, isopropanol, butanol,isobutanol and tert-butanol.

Bases (deprotonating agents) which can be employed when carrying outprocess (B) according to the invention are all customary protonacceptors. The following can preferably be used: the oxides, hydroxidesand carbonates of alkali metals and alkaline earth metals, such assodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide,sodium carbonate, potassium carbonate and calcium carbonate, all ofwhich can also be employed in the presence of phase-transfer catalystssuch as, for example, triethylbenzylammonium chloride,tetrabutylammonium bromide, Adogen 464 (=methyltrialkyl(C₈–C₁₀)ammoniumchloride) or TDA 1 (=tris-(methoxyethoxyethyl)-amine). Alkali metalssuch as sodium or potassium can furthermore be used. Amides and hydridesof alkali metals and alkaline earth metals, such as sodium amide, sodiumhydride and calcium hydride are further possible materials which can beused, as are, moreover, alkali metal alkoxides such as sodium methoxide,sodium ethoxide and potassium tert-butoxide.

When carrying out process (B) according to the invention, the reactiontemperatures can be varied within a substantial range. In general, theprocess is carried out at temperatures of between −80° C. and 180° C.,preferably between −50° C. and 120° C.

Process (B) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (B) according to the invention, the reactantsof the formula (II) and the deprotonating bases are generally employedin approximately twice the equimolar amounts. However, it is possible touse one or the other reactants in a larger excess (up to 3 mol).

Process (C-α) is characterized in that compounds of the formulae (I-1-a)to (I-2-a) are in each case reacted with carboxylic acid halides of theformula (IV), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

Diluents which can be employed in process (C-α) according to theinvention are all solvents which are inert to the acid halides. Thefollowing can preferably be used: hydrocarbons such as benzine, benzene,toluene, xylene and tetralin, furthermore halogenohydrocarbons such asmethylene chloride, chloroform, carbon tetrachloride, chlorobenzene ando-dichlorobenzene, moreover ketones such as acetone and methyl isopropylketone, furthermore ethers such as diethyl ether, tetrahydrofuran anddioxane, in addition carboxylic esters such as ethyl acetate, nitrilessuch as acetonitrile, or else strongly polar solvents such asdimethylformamide, dimethylacetamide, dimethyl sulphoxide andsulpholane. If the acid halide is sufficiently stable to hydrolysis, thereaction may also be carried out in the presence of water.

Suitable acid binders when carrying out the reaction in accordance withprocess (C-α) according to the invention are all customary acidacceptors. The following can preferably be used: tertiary amines such astriethylamine, pyridine, diazabicyclooctane (DABCO),diazabicycloundecene (DBU), diazabicyclononene (DBN), Hünig Base andN,N-dimethyl-anilin, furthermore alkali metal oxides such as magnesiumoxide and calcium oxide, moreover alkali metal carbonates and alkalineearth metal carbonates such as sodium carbonate, potassium carbonate andcalcium carbonate, and alkali metal hydroxides such as sodium hydroxideand potassium hydroxide.

When carrying out process (C-α) according to the invention, the reactiontemperatures may be varied within a substantial range. In general, theprocess is carried out at temperatures of between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out process (C-α) according to the invention, the startingmaterials of the formulae (I-1-a) to (I-2-a) and the carboxylic acidhalide of the formula (IV) are generally in each case used inapproximately equivalent amounts. However, it is also possible to employthe carboxylic acid halides in a larger excess (of up to 5 mol). Work-upis carried out by customary methods.

Process (C-β) is characterized in that compounds of the formulae (I-1-a)to (I-2-a) are reacted with carboxylic anhydrides of the formula (V), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Diluents which can be used in process (C-β) according to the inventionare preferably those diluents which are also preferably suitable whenacid halides are used. Besides, a carboxylic anhydride used in excessmay also simultaneously act as the diluent.

Suitable acid binders which are optionally added in process (C-β) arepreferably those acid binders which are also preferably suitable whenacid halides are used.

When carrying out process (C-β), the reaction temperatures can be variedwithin a substantial range. In general, the process is carried out attemperatures of between −20° C. and +150° C., preferably between 0° C.and 100° C.

When carrying out process (C-β) according to the invention, the startingmaterials of the formulae (I-1-a) to (I-2-a) and the carboxylicanhydride of the formula (V) are generally employed in each case inapproximately equivalent amounts. However, it is also possible to employthe carboxylic anhydride in a larger excess (of up to 5 mol). Work-up iscarried out by customary methods.

In general, a procedure is followed in which diluent, excess carboxylicanhydride and the carboxylic acid which forms are removed bydistillation or by washing with an organic solvent or with water.

Process (D) is characterized in that compounds of the formulae (I-1-a)to (I-2-a) are reacted in each case with chloroformic esters orchloroformic thioesters of the formula (VII), if appropriate in thepresence of a diluent and if appropriate in the presence of acid binder.

Suitable acid binders for the reaction in accordance with process (D)according to the invention are all customary acid acceptors. Thefollowing can preferably be used: tertiary amines such as triethylamine,pyridine, DABCO, DBU, DBA, Hünig base and N,N-dimethyl-anilin,furthermore alkali metal oxides such as magnesium oxide and calciumoxide, moreover alkali metal carbonates and alkaline earth metalcarbonates such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides such as sodium hydroxide andpotassium hydroxide.

Diluents which can be employed in process (D) according to the inventionare all solvents which are inert to the chloroformic esters orchloroformic thioesters. The following can preferably be used:hydrocarbons such as benzine, benzene, toluene, xylene and tetraline,furthermore halogeno-hydrocarbons such as methylene chloride,chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene,moreover ketones such as acetone and methyl isopropyl ketone,furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane,in addition carboxylic esters such as ethyl acetate, nitriles such asacetonitrile and also strongly polar solvents such as dimethylformamide,dimethylacetamide, dimethyl sulphoxide and sulpholane.

When carrying out process (D) according to the invention, the reactiontemperatures can be varied within a substantial range. If the process iscarried out in the presence of a diluent and of an acid binder, thereaction temperatures are generally between −20° C. and +100° C.,preferably between 0° C. and 50° C.

Process (D) according to the invention is generally carried out underatmospheric pressure.

When carrying out process (D) according to the invention, the startingmaterials of the formulae (I-1-a) to (I-2-a) and the correspondingchloroformic ester or chloroformic thioester of the formula (VI) aregenerally used in each case in approximately equivalent amounts.However, it is also possible to employ one or the other reactant in alarger excess (of up to 2 mol). Work-up is carried out by customarymethods. In general, a procedure is followed in which the salts whichhave precipitated are removed and the reaction mixture which remains isconcentrated by stripping off the diluent.

Process (E) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are reacted in each casewith compounds of the formula (VII) in the presence of a diluent and, ifappropriate, in the presence of an acid binder.

In preparation process (E), approximately 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (VII) is reacted atfrom 0 to 120° C., preferably at from 20 to 60° C., per mole of startingcompound of the formulae (I-1-a) to (I-2-a).

Suitable diluents which are optionally added are all inert polar organicsolvents such as nitrites, esters, ethers, amides, sulphones,sulphoxides, but also halogenoalkanes.

Substances which are preferably employed are acetonitrile, ethylacetate, dimethyl sulphoxide, tetrahydrofuran, dimethylformamide ormethylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (I-1-a)to (I-2-a) by addition of strong deprotonating agents such as, forexample, sodium hydride or potassium tertiary-butylate, the furtheraddition of acid binders can be dispensed with.

If acid binders are employed, then customary inorganic or organic basesare suitable, with sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine being mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. Work-up iscarried out by customary methods.

Process (F) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are reacted in each casewith sulphonyl chloride of the formula (VIII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In preparation process (F), approximately 1 mol of sulphonyl chloride ofthe formula (VIII) is reacted at from −20 to 150° C., preferably at from20 to 70° C., per mole of starting compound of the formulae (I-1-a) to(I-2-a).

Suitable diluents which are optionally added are all inert polar organicsolvents such as nitriles, esters, ethers, amides, nitriles, sulphones,sulphoxides or halogenated hydrocarbons such as methylene chloride.

Substances which are preferably employed are acetonitrile, ethylacetate, dimethyl sulphoxide, tetrahydrofuran, dimethylformamide,methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds.(I-1-a) to (I-2-a) is synthesized by addition of strong deprotonatingagents (such as, for example, sodium hydride or potassiumtertiary-butoxide), the further addition of acid binders can bedispensed with.

If acid binders are employed, customary inorganic or organic bases aresuitable, with sodium hydroxide, sodium carbonate, potassium carbonate,pyridine and triethylamine being mentioned by way of example.

The reaction can be carried out under atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. Work-up iscarried out by customary methods.

Process (G) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are reacted in each casewith phosphorus compounds of the formula (IX), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

In preparation process (G), 1 to 2, preferably 1 to 1.3, mole of thephosphorus compound of the formula (IX) are reacted at temperatures ofbetween −40° C. and 150° C., preferably between −10 and 110° C., permole of the compounds (I-1-a) to (I-2-a) in order to obtain compounds ofthe formulae (I-1-e) to (I-2-e).

Suitable diluents which are optionally added are all inert polar organicsolvents such as ethers, amides, nitrites, alcohols, sulphides,sulphones, sulphoxides and the like.

Substances which are preferably employed are acetonitrile, dimethylsulphoxide, tetrahydrofuran, dimethylformamide, methylene chloride.

Suitable acid binders which are optionally added are customary inorganicor organic bases such as hydroxides, carbonates or amines. Exampleswhich may be mentioned are sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine, triethylamine.

The reaction can be carried out under atmospheric pressure or underelevated pressure, preferably under atmospheric pressure. Work-up iscarried out by customary methods of organic chemistry. The resulting endproducts are preferably purified by crystallization, chromatography orby what is known as “incipient distillation”, that is to say removal ofthe volatile components in vacuo.

Process (H) is characterized in that compounds of the formulae (I-1-a)to (I-2-a) are reacted with metal hydroxides or metal alkoxides of theformula (X) or amines of the formula (XI), if appropriate in thepresence of a diluent.

Diluents which can be employed in process (I) according to the inventionare, preferably, ethers such, as tetrahydrofuran, dioxane, diethylether, or else alcohols such as methanol, ethanol, isopropanol, but alsowater.

Process (H) according to the invention is generally carried out underatmospheric pressure.

In general, the reaction temperatures are between −20° C. and 100° C.,preferably between 0° C. and 50° C.

Process (I) according to the invention is characterized in thatcompounds of the formulae (I-1-a) to (I-2-a) are reacted in each casewith compounds of the formula (XII) (I-α), if, appropriate in thepresence of a diluent and if appropriate in the presence of a catalyst,or (I-β) with compounds of the formula (XIII), if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder.

When carrying out preparation process (I-α), approximately 1 mol ofisocyanate of the formula (XII) is reacted at from 0 to 100° C.,preferably at from 20 to 50° C., per mole of starting compound of theformulae (I-1-a) to (I-2-a).

Suitable diluents which are optionally added are all inert organicsolvents, such as ethers, amides, nitrites, sulphones, sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Catalysts which can be employed very advantageously are organotincompounds such as, for example, dibutyltin dilaurate. The process ispreferably carried out under atmospheric pressure.

When carrying out preparation process (I-β), approximately 1 mol ofcarbamoyl chloride of the formula (XIII) is reacted at from −20 to 150°C., preferably at from 0 to 70° C., per mole of starting compound of theformulae (I-1-a) to (I-2-a).

Suitable diluents which are optionally added are all inert polar organicsolvents such as nitriles, esters, ethers, amides, sulphones,sulphoxides or halogenated hydrocarbons.

The substances which are preferably employed are acetonitrile, ethylacetate, dimethyl sulphoxide, tetrahydrofuran, dimethylformamide ormethylene chloride.

If, in a preferred embodiment, the enolate salt of the compound (I-1-a)to (I-2-a) is synthesized by adding strong deprotonating agents (suchas, for example, sodium hydride or potassium tertiary-butoxide), thefurther addition of acid binders can be dispensed with.

The active compounds are suitable for controlling animal pests, inparticular insects, arachnids and nematodes found in agriculture, inforests, in the protection of stored products and materials, and in thehygiene sector, while being well tolerated by plants and exhibiting afavourable toxicity to warm-blooded species. They can preferably beemployed as crop protection agents. They are active against normallysensitive and resistant species and against all individual developmentalstages. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus,Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp.,Schistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp.,Damalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus, Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodernaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon soistitialis, Costelytra zealandica, Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp., Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis,Ceratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

The plant-parasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

If appropriate, the compounds according to the invention, in specificconcentrations or at specific application rates, can also be used asherbicides and microbicides, for example as fungicides, antimycotics andbactericides. If appropriate, they may also be used as intermediates orprecursors for the synthesis of further active compounds.

All plants and plant parts can be treated in accordance with theinvention. Plants are understood, in the present context, as meaning allplants and plant populations such as desired and undesired wild plantsor crop plants (including naturally occurring crop plants). Crop plantsmay be plants which can be obtained by conventional breeding andoptimization methods or else by biotechnological and recombinant methodsor combinations of these methods, including the transgenic plants andthe plant varieties which can be protected or which cannot be protectedby Plant Breeders' Rights. Plant parts are understood as meaning allaerial and subterraneous parts and organs of the plants, such as shoot,leaf, flower and root, with leaves, needles, stems, stalks, flowers,fruiting bodies, fruits and seeds and also roots, tubers and rhizomesbeing mentioned by way of example. The plant parts also includeharvested material and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, shoots and seeds.

The treatment according to the invention of the plants and plant partswith the active compounds is affected directly or by acting on theirenvironment or the surroundings in which they grow or in which they arestored, using customary treatment methods, for example by immersion,spraying, atomizing, forging, spreading, brushing on and, in the case ofpropagation material, in particular seeds, furthermore by coating withone or more coats.

The active compounds can be converted into the customary formulationssuch as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspended emulsionconcentrates, natural and synthetic materials impregnated with activecompounds, and microencapsulations and polymeric substances.

These formulations are prepared in the known manner, for example bymixing the active compounds with extenders, that is to say liquidsolvents and/or solid carriers, if appropriate using surfactants, thatis to say emulsifiers and/or dispersants and/or foam formers.

If water is used as extender, it is also possible, for example, to useorganic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatics such as xylene, toluene, or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons, such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons, such as cyclohexane, or paraffins, for example mineral oilfractions, mineral and vegetable oils, alcohols such as butanol orglycol and their ethers and esters, ketones such as acetone, methylethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polarsolvents such as dimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are:

for example, ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals such as highly disperse silica,alumina and silicates; suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite, dolomite, and synthetic granules of inorganic ororganic meals and granules of organic material such as sawdust, coconutshells, maize cobs and tobacco stalks; suitable emulsifiers and/or foamformers are: for example, non-ionic and anionic emulsifiers such aspolyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers,for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates; suitabledispersants are: for example, lignin-sulphite waste liquors andmethylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic polymersin the form of powders, granules or latices such as gum arabic,polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such ascephalins and lecithins and synthetic phospholipids may be used in theformulations. Other additives may be mineral and vegetable oils.

Colorants such as inorganic pigments, for example iron oxide, titaniumoxide, Prussian Blue, and organic dyestuffs such as alizarin, azo andmetal phthalocyanin dyes and micronutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc may be used.

In general, the formulations comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in theirformulations, may also be used in a mixture with known fungicides,bactericides, acaridices, nematicides or insecticides, for example towiden the spectrum of action or to prevent the build-up of resistance.In many cases, synergistic effects result, i.e. the activity of themixture exceeds the activity of the individual components.

Examples of suitable components in mixtures are the following compounds:

Fungicides

aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvone, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezin,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamin, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxyde, ferbam, ferimzone, fluazinam, flumetover, fluoromid,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolan, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulphocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiine,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole,prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole,propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamid, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

-   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,-   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,    (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,    (E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,    1-isopropyl    {2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbonate-   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone    O-(phenylmethyl)-oxime,-   1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,-   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,-   1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,-   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,-   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,-   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,-   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol,-   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,-   2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,-   2,6-dichloro-5-(methylthio)-4-pyrimidinyl thiocyanate,-   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,-   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,-   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,-   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,-   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,-   2-aminobutane,-   2-bromo-2-(brommethyl)-pentanedinitrile,-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,-   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,-   2-phenylphenol(OPP),-   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,-   3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,-   3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,-   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,-   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,-   4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,-   8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4,5]decane-2-methanamine,-   8-hydroxyquinolin sulphate,-   9H-xanthene-9-carboxylic acid 2-[(phenylamino)-carbonyl]-hydrazide,-   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophene    dicarboxylate,-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,-   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine    hydrochloride,-   Ethyl [(4-chlorophenyl)-azo]-cyanoacetate,-   potassium hydrogen carbonate,-   sodium methane tetrathiolate,-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,-   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,-   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,-   N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,-   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,-   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,-   N-(6-methoxy)-3-pyrdinyl)-cyclopropanecarboxamide,-   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,-   N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′methoxy-methanimidamide,-   sodium N-formyl-N-hydroxy-DL-alaninate,-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   O-methyl S-phenyl phenylpropylphosphoramidothioate,-   S-methyl 1,2,3-benzothiadiazole-7-carbothioate,-   spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,-   4-[3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, oc-thilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, bistrifluron,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, chromafenozide, cisresmethrin, cispermethrin,clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,dimethylvinphos, diofenolan, disulfoton, docusate-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomophthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate,fubfenprox, furathiocarb,

granulosis viruses

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses

lambda-cyhalothrin, lufenuron

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,mevinphos, milbemectin, milbemycin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron

omethoate, oxamyl, oxydemethon M

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,propargite, propoxur, prothiofos, prothoate, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,pyriproxyfen,

quinalphos,

ribavirin

salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep,suiprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid,thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,triarathene, triazamate, triazophos, triazuron, trichlophenidine,trichlorfon, triflumuron, trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii

YI 5302

zeta-cyperrnethrin, zolaprofos

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]2,2-dimethylcyclopropanecarboxylate

(3-phenoxyphenyl)-methyl 2,2,3,3-tetramethylcyclopropanecarboxylate

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazin-2(1H)-imine

-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole-   2-(acetyloxy)-3-dodecyl-1,4-naphthalenedione-   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluorethoxy)-phenyl]-amino]-carbonyl]-benzamide-   3-methylphenyl propylcarbamate-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone-   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorphenyl)-3(2H)-pyridazinone-   Bacillus thuringiensis strain EG-2348-   [2-benzoyl-1-(1,1-dimethylethyl)]-benzohydrazide-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl-ester    butanoate-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde-   ethyl    [2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine-   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazine dicarbothioamide-   N-methyl-N′-2-propenyl-1,2-hydrazine dicarbothioamide-   O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate-   N-cyanomethyl-4-trifluoromethyl-nicotinamide-   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)-propoxy]-benzene

A mixture with other known active compounds such as herbicides or withfertilizers and growth regulators is also possible.

When employed as insecticides, the active compounds according to theinvention, in their commercially available formulations and in the useforms prepared from these formulations, may furthermore be present in amixture with synergists. Synergists are compounds by which the action ofthe active compounds is increased without it being necessary for thesynergist added to be active itself.

The active compound content of the use forms prepared from thecommerically available formulations can vary within wide ranges. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

They are applied in a customary manner adapted to suit the use forms.

When used against hygiene and stored-product pests, the active compoundis distinguished by outstanding residual action on wood and clay and bygood stability to alkali on limed substrates.

As already mentioned above, all plants and their parts may be treated inaccordance with the invention. In a preferred embodiment, plant speciesand plant varieties which occur in the wild or which have been obtainedby conventional biological breeding methods, such as hybridization orprotoplast fusion, and parts of these plant species and plant varietiesare treated. In another preferred embodiment, transgenic plants andplant varieties which have been obtained by genetic engineering methods,if appropriate in combination with conventional methods (geneticmodified organisms), and parts of these plants and plant varieties aretreated. The term “parts” and “parts of plants” or “plant parts” hasbeen illustrated above.

Plants which are especially preferably treated in accordance with theinvention are those of the plant varieties which are commerciallyavailable or in use. Plant varieties are understood as meaning plantswith novel properties (“traits”) which have been bred by conventionalbreeding, by mutagenesis and also be recombinant DNA techniques. Theycan take the form of varieties, biotypes and genotypes.

Depending on the plant species or plant varieties, their location andgrowth conditions (soils, climate, vegetation period, nutrition),superadditive (“synergistic”) effects may also occur as a result of thetreatment in accordance with the invention. Thus, for example, reducedapplication rates and/or a widened spectrum of action and/or anincreased action of the substances and compositions which can be used inaccordance with the invention, better plant growth, increased toleranceto high or low temperatures, increased tolerance to drought or to wateror soil salinity, increased flowering performance, facilitatedharvesting, accelerated maturation, higher yields, higher quality and/orhigher nutritional value of the harvested products, better storabilityand/or processability of the harvested products are possible, whichexceed the actual effects to be expected.

The preferred transgenic plants or plant varieties (obtained byrecombinant methods) to be treated in accordance with the inventioninclude all plants which, owing to modification by recombinant means,contain genetic material which imparts particular advantageous valuabletraits to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salinity, increased floweringperformance, facilitated harvesting, accelerated maturation, higheryields, higher quality and/or higher nutritional value of the harvestedproducts, better storability and/or processability of the harvestedproducts. Other especially emphasized examples of such traits are anincreased defence of the plants against animal and microbial pests suchas against insects, mites, phytopathogenic fungi, bacteria and/orviruses, and an increased tolerance of the plants to certain herbicidalactive compounds. Examples of transgenic plants which may be mentionedare important crop plants such as cereals (wheat, rice), maize, soya,potato, cotton, oil seed rape and fruit plants (with the fruits apples,pears, citrus fruit and grapes), with particular emphasis being placedon maize, soya, potato, cotton and oil seed rape. Traits which areparticularly emphasized are the increased defence of the plants againstinsects by toxins formed in the plants, in particular those which aregenerated by the genetic material from Bacillus thuringiensis (forexample, by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA,CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) in theplants (hereinbelow “Bt plants”). Other traits which are particularlyemphasized are the increased defence of plants against fungi, bacteriaand viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Other traits which are furthermoreparticularly emphasized are the increased tolerance of the plants tocertain herbicidal active compounds, for example imidazolinones,sulphonyl ureas, glyphosate or phosphinothricin (for example “PAT”gene). The genes which impart each of the desired traits may also occurin combination with each other in the transgenic plants. Examples of “Btplants” which may be mentioned are varieties of maize, cotton, soya andpotato which are commercially available under the trade names YIELDGARD® (for example, maize, cotton, soya), KnockOut® (for example maize),StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) andNewLeaf® (potato). Examples of herbicide-tolerant plants which may bementioned are varieties of maize, cotton and soya which are commerciallyavailable under the trade names Roundup Ready® (tolerance to glyphosate,for example maize, cotton, soya), Liberty Link® (tolerance tophosphinothricin, for example oil seed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonyl ureas, for examplemaize). Herbicide-resistant plants (bred conventionally for herbicidetolerance) which may also be mentioned are the varieties which arecommercially available under the name Clearfield® (for example maize).Naturally, these statements also apply to plant varieties which will bedeveloped in the future or which will be marketed in the future andwhich have these genetic traits, or genetic traits to be developed inthe future.

The plants stated can be treated particularly advantageously inaccordance with the invention with the compounds of the general formulaI or the active compound mixtures according to the invention. Thepreferred ranges stated above for the active compounds or mixtures alsoapply to the treatment of these plants. The treatment of plants with thecompounds or mixtures specifically stated in the present text may beparticularly emphasized.

The active compounds according to the invention not only act againstplant, hygiene and stored-product pests, but also, in the veterinarymedicine sector, against animal parasites (ectoparasites) such as hardticks, soft ticks, scab mites, harvest mites, flies (stinging andlicking), parasitic fly larvae, lice, hair lice, bird lice and fleas.These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

From the order Diptera and the suborders Nematocerina and Brachycerina,for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp.,Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida, for example, Cimex spp., Triatomaspp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattella germanica, Supella spp.

From the subclass of the Acaria (Acarida) and the orders of theMetastigmata and Mesostigmata, for example, Argas spp., Ornithodorusspp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp.,Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.,Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp.,Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention arealso suitable for controlling arthropodes which attack agriculturallivestock such as, for example, cattle, sheep, goats, horses, pigs,donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese,honeybees, other domestic animals such as, for example, dogs, cats, cagebirds, aquarium fish and what are known as experimental animals such as,for example, hamsters, guineapigs, rats and mice. By controlling thesearthropodes, it is intended to reduce deaths and reduced performance (inmeat, milk, wool, hides, eggs, honey and the like) so that more economicand simpler animal keeping is possible by employing the active compoundsaccording to the invention.

The active compounds according to the invention are applied in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, drinks, drenches, granules,pastes, bolisis, the feed-through method, suppositories, by parenteraladministration such as, for example, by injections (intramuscular,subcutaneous, intravenous, intraperitoneal and the like), implants, bynasal application, by dermal application in the form of, for example,immersing or bathing (dipping), spraying, pouring-on and spotting-on,washing, dusting and with the aid of shaped articles comprising activecompound, such as collars, ear marks, tail marks, limb bands, halters,marking devices and the like.

When used for livestock, poultry, domestic animals and the like, theactive compounds of the formula (I) can be used as formulations (forexample powders, emulsions, flowables) comprising the active compoundsin an amount of from 1 to 80% by weight, either directly or after 100 to10 000-fold dilution, or they may be used as a chemical bath.

Moreover, it has been found that the compound according to the inventionhas a potent insecticidal action against insects which destroyindustrial materials.

The following insects may be mentioned by way of example and bypreference, but without limitation:

Beetles such as

Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobiumrufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobiusmollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctusplanicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale,Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus,Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec.Dinoderus minutus.

Hymenoptera such as

Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.

Termites such as

Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola,Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermeslucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis,Coptoternes formosanus.

Bristle tails such as Lepisma saccharina.

Industrial materials in the present context are understood as meaningnon-live materials such as, preferably, polymers, adhesives, glues,paper and board, leather, wood, tin products and paints.

The material to be protected from insect attack is very especiallypreferably wood and timber products.

Wood and timber products which can be protected by the agent accordingto the invention or mixtures comprising it are to be understood asmeaning, for example:

Construction timber, wooden beams, railway sleepers, bridge components,jetties, vehicles made of wood, boxes, pallets, containers, telephonepoles, wood lagging, windows and doors made of wood, plywood, chipboard,joinery, or timber products which quite generally are used in houseconstruction or building joinery.

The active compounds can be used as such, in the form of concentrates orgenerally customary formulations such as powders, granules, solutions,suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds with at least one solvent ordiluent, emulsifier, dispersant and/or binder or fixative, waterrepellent, if desired desiccants and UV stabilizers, and if desiredcolorants and pigments and other processing aids.

The insecticidal compositions or concentrates used for the protection ofwood and timber products comprise the active compound according to theinvention in a concentration of from 0.0001 to 95% by weight, inparticular from 0.001 to 60% by weight.

The amount of the compositions or concentrates employed depends on thespecies and the abundance of the insects and of the medium. The optimalquantity to be employed can be determined in each case upon applicationby test series. In general, however, it will suffice to employ from0.0001 to 20% by weight, preferably from 0.001 to 10% by weight, of theactive compound, based on the material to be protected.

A suitable solvent and/or diluent is an organochemical solvent orsolvent mixture and/or an oily or oil-type organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water and, if appropriate, an emulsifierand/or wetter.

Organochemical solvents which are preferably employed are oil oroil-type solvents with an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. Such oily and oil-typesolvents which are insoluble in water and of low volatility and whichare used are suitable mineral oils or their aromatic fractions ormineral-oil-containing solvent mixtures, preferably white spirit,petroleum and/or alkyl benzene.

Mineral oils which are advantageously used are those with a boilingrange of from 170 to 220° C., white spirit with a boiling range of from170 to 220° C., spindle oil with a boiling range of from 250 to 350° C.,petroleum and aromatics with a boiling range of from 160 to 280° C., oilof turpentine, and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boilingrange of from 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of from 180 to 220° C.and/or spindle oil and/or monochloronaphthalene, preferablyα-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility and with anevaporation number of above 35 and a flash point of above 30° C.,preferably above 45° C., can be replaced in part by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flash point ofabove 30° C., preferably above 45° C., and that theinsecticide/fungicide mixture is soluble or emulsifiable in this solventmixture.

In a preferred embodiment, some of the organochemical solvent or solventmixture is replaced by an aliphatic polar organochemical solvent orsolvent mixture. Aliphatic organochemical solvents which containhydroxyl and/or ester and/or ether groups are preferably used, such as,for example, glycol ethers, esters or the like.

Organochemical binders used for the purposes of the present inventionare the synthetic resins and/or binding drying oils which are known perse and which can be diluted in water and/or dissolved or dispersed oremulsified in the organochemical solvents employed, in particularbinders composed of, or comprising, an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenol resin, hydrocarbon resin such as indene/coumarone resin,silicone resin, drying vegetable and/or drying oils and/or physicallydrying binders based on a natural and/or synthetic resin.

The synthetic resin employed as binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bitumenous substances mayalso be used as binders, in amounts of up to 10% by weight. In addition,colorants, pigments, water repellents, odour-masking agents, andinhibitors or anticorrosive agents and the like, all of which are knownper se, can be employed.

In accordance with the invention, the composition or the concentratepreferably comprises, as organochemical binder, at least one alkyd resinor modified alkyd resin and/or a drying vegetable oil. Alkyd resinswhich are preferably used in accordance with the invention are thosewith an oil content of over 45% by weight, preferably 50 to 68% byweight.

Some or all of the abovementioned binder can be replaced by a fixative(mixture) or a plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds, and also crystallizationor precipitation. They preferably replace from 0.01 to 30% of the binder(based on 100% of the binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate,phosphoric esters such as tributyl phosphate, adipic esters such asdi-(2-ethylhexyl)-adipate, stearates such as butyl stearate or amylstearate, oleates such as butyl oleate, glycerol ethers orhigher-molecular-weight glycol ethers, glycerol esters andp-toluenesulphonic esters.

Fixatives are based chemically on polyvinyl alkyl ethers such as, forexample, polyvinyl methyl ether, or ketones such as benzophenone andethylene benzophenone.

Other suitable solvents or diluents are, in particular, also water, ifappropriate in a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective timber protection is achieved by industrial-scaleimpregnating processes, for example the vacuum, double-vacuum orpressure processes.

If appropriate, the compositions which are ready for use canadditionally comprise further insecticides and, if appropriate,additionally one or more fungicides.

Additional components in mixtures which are suitable are, preferably,the insecticides and fungicides stated in WO 94/29 268. The compoundsstated in this document are expressly part of the present application.

Very especially preferred components in mixtures which can be used areinsecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxideand triflumuron, and fungicides such as epoxyconazole, hexaconazole,azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole,imazalil, dichlorfluanid, tolylfluanid, 3-iod-2-propinyl butylcarbamate,N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazolin-3-one.

The compounds according to the invention can simultaneously also beemployed for protecting objects which come into contact with salt waterand brackish water, such as hulls, screens, nets, buildings, mooringsand signalling systems, from fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells andspecies from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent residence in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramiumsp., fouling by sessile Entomostraka groups, which come under thegeneric term Cirripedia (cirriped crustaceans), is of particularimportance.

Surprisingly, it has now been found that the compounds according to theinvention, alone or in combination with other active compounds, have anoutstanding antifouling action.

Using the compounds according to the invention, alone or in combinationwith other active compounds, the use of heavy metals such as, forexample, in bis(trialkyltin) sulphides, tri-n-butyltin laurate,tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl-(bispyridine)-bismuth chloride, tri-n-butyltin fluoride,manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts ofpyridine-2-thiol 1-oxide, bisdimethyldithiocarbamoylzincethylenebisthiocarbamate, zinc oxide, copper(I)ethylene-bisthiocarbamate, copper thiocyanate, copper naphthenate andtributyltin halides can be dispensed with, or the concentration of thesecompounds can be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionallycomprise other active compounds, preferably algicides, fungicides,herbicides, molluscicides, or other antifouling active compounds.

Preferably suitable components in combination with the antifoulingcompositions according to the invention are:

Algicides such as

2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

Fungicides such as

benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as

azaconazole, cyproconazole, epoxyconazole, hexaconazole, metconazole,propi-conazole and tebuconazole;

Molluscicides such as

fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarb andtrimethacarb; or traditional antifouling active compounds such as

4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-di-methylthiocarbamoylthio)-5-nitrothiazyl, potassiumsalts, copper salts, sodium salts and zinc salts of pyridine-2-thiol1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleinimide.

The antifouling compositions used comprise the active compound accordingto the invention of the compounds according to the invention in aconcentration of from 0.001 to 50% by weight, in particular 0.01 to 20%by weight.

Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730–732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds andthe insecticidal active compounds according to the invention,antifouling paints comprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system, in particular in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils such as linseed oil, resin esters or modifiedhardened resins in combination with tar or bitumens, asphalt and epoxycompounds, small amounts of chlorine rubber, chlorinated polypropyleneand vinyl resins.

If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably soluble in salt water. Paintsmay furthermore comprise materials such as kolophonium to allowcontrolled release of the active compounds.

Furthermore, the paints may comprise plasticizers, modifiers whichaffect the Theological properties and other conventional constituents.The compounds according to the invention or the abovementioned mixturesmay also be incorporated into self-polishing antifouling systems.

The active compounds are also suitable for controlling animal pests, inparticular insects, arachnids and mites, which are found in enclosedspaces such as, for example, dwellings, factory halls, offices, vehiclecabins and the like. They can be employed in domestic insecticideproducts for controlling these pests, either alone or in combinationwith other active compounds and auxiliaries. They are effective againstsensitive and resistant species and against all developmental stages.These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

Application in the field of domestic insecticides is affected alone orin combination with other suitable active compounds such as phosphoricesters, carbamates, pyrethroides, growth regulators or active compoundsfrom other known classes of insecticides.

They are used as aerosols, pressure-free spray products, for examplepump and atomizer sprays, automatic fogging systems, foggers, foams,gels, evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free or passive evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

The active compounds according to the invention can also be used asdefoliants, desiccants, haulm killers and, especially, as weedkillers.By weeds, in the broadest sense, are to be understood all plants whichgrow in locations where they are undesired. Whether the substancesaccording to the invention act as total or selective herbicides dependsessentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia,Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus,Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium,Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus,Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha,Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum,Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola,Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis,Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca,Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis,Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina,Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis,Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera,Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum,Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria,Sorghum.

Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

Depending on the concentration, the compounds are suitable for totalweed control, for example on industrial terrain and rail tracks, and onpaths and areas with or without tree stands. Equally, the compounds canbe employed for controlling weeds in perennial crops, for exampleforests, ornamental tree plantings, orchards, vineyards, citrus groves,nut orchards, banana plantations, coffee plantations, tea plantations,rubber plantations, oil palm plantations, cocoa plantations, soft fruitplantings and hop fields, in lawns, turf and pastures, and for selectiveweed control in annual crops.

The compounds of the formula (I) according to the invention show apotent herbicidal activity and a broad spectrum of action when used onthe soil and on aerial plant parts. To a certain extent, they are alsosuitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothpre- and post-emergence.

At certain concentrations or application rates, the active compoundsaccording to the invention can also be used for controlling animal pestsand fungal or bacterial plant diseases. If appropriate, they can also beused as intermediates or precursors for the synthesis of further activecompounds.

The active compounds can be converted into the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusts, pastes, soluble powders, granules, suspoemulsion concentrates,natural and synthetic materials impregnated with active compound, andmicroencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers.

If water is used as an extender, organic solvents can, for example, alsobe used as cosolvents. Liquid solvents which are mainly suitable are:aromatics such as xylene, toluene or alkylnaphthalenes, chlorinatedaromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons such ascyclohexane or paraffins, for example petroleum fractions, mineral andvegetable oils, alcohols such as butanol or glycol as well as theirethers and esters, ketones such as acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, and water.

Suitable solid carriers are: for example, ammonium salts and groundnatural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as highly disperse silica, alumina and silicates; suitablesolid carriers for granules are: for example, crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic meals, and granulesof organic material such as sawdust, coconut shells, maize cobs andtobacco stalks; suitable emulsifiers and/or foam formers are: forexample, non-ionic and anionic emulsifiers, such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,arylsulphonates and protein hydrolysates; suitable dispersants are: forexample, lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices such as gum arabic,polyvinyl alcohol and polyvinyl acetate, or else natural phospholipidssuch as cephalins and lecithins, and synthetic phospholipids can be usedin the formulations. Further additives can be mineral and vegetableoils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention,as such or in the form of their formulations, can also be used asmixtures with known herbicides and/or with substances which improve thecrop plant tolerance (“safeners”), ready mixes or tank mixes beingpossible. Thus, mixtures with weed killers comprising one or more knownherbicides and a safener are also possible.

Suitable herbicides for the mixtures are known herbicides, for example

acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos,asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin(-ethyl), benfuresate, bensulfuron (-methyl), bentazone, benzfendizone,benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox,bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor,butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim,carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben,chloridazon, chlorimuron (-ethyl), chlomitrofen, chlorsulfuron,chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim,clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid,clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine,cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl),2,4-D, 2,4-DB, desmedipham, di-allate, dicamba, dichlorprop (-P),diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat,diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor,dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid,diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb,ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide,flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam,fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet,flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn,flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl),flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol,flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron,glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen,haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin,imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop,mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron,metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron,metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide,napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin,oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen,paraquat, pelargonic acid, pendi-methalin, pendralin, pentoxazone,phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyiibuticarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, tri-allate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

Furthermore, safeners which are suitable for the mixtures are knownsafeners, for example:

AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cyometrinil, 2,4-D,DKA-24, dichlormid, dymron, fenclorim, fenchlorazol (-ethyl), flurazole,fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P),mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292, R-29148.

Mixtures with other known active compounds such as fungicides,insecticides, acaricides, nematicides, bird repellants, plant nutrientsand soil conditioners are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or spreading.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants. They can also be incorporatedinto the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 1 g and 10 kg of active compound perhectare of soil surface, preferably between 5 g and 5 kg per ha.

The substances according to the invention exhibit a potent microbicidalaction and can be employed for controlling undesired microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

Fungicidal agents are employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericidal agents are employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

Pythium species, such as, for example, Pythium ultimum;

Phytophthora species, such as, for example, Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonosporahumuli or Pseudoperonospora cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P.brassicae;

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;

Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P.graminea (conidial form: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus(conidial form: Drechslera, syn: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus;

Puccinia species, such as, for example, Puccinia recondita;

Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilagoavenae;

Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum;

Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae; and

Pseudocercosporella species, such as, for example, Pseudocercosporellaherpotrichoides.

The active compounds according to the invention also exhibit a potentstrengthening effect in plants. They are therefore suitable formobilizing the plants' intrinsic defences against attack by undesiredmicroorganisms.

Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances whichare capable of stimulating the defence system of plants in such a waythat the treated plants, when subsequently inoculated with undesiredmicroorganisms, develop a high degree of resistance to thesemicroorganisms.

Undesired microorganisms are understood as meaning, in the present case,phytopathogenic fungi, bacteria and viruses. The substances according tothe invention can thus be employed to protect plants against infectionby the abovementioned pathogens within a specific period post-treatment.The period within which protection is brought about generally extendsfrom 1 to 10 days, preferably 1 to 7 days, after the treatment of theplants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of aerial plant parts, of propagation stock and seeds, and ofthe soil.

The active compounds according to the invention are also suitable forincreasing the yield. Moreover, they have a low degree of toxicity andare well tolerated by plants.

If appropriate, the active compounds according to the invention can alsobe employed in specific concentrations and application rates asherbicides, for influencing plant growth, and for controlling animalpests. If appropriate, they may also be employed as intermediates andprecursors for the synthesis of further active compounds.

In the protection of materials, the substances according to theinvention can be employed for protecting industrial materials againstinfection with, and destruction by, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-live materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be glues, sizers, paper and board, textiles, leather,wood, paints and synthetic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the multiplication of microorganisms, may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably glues, sizers, paper and board, leather, wood,paints, cooling lubricants and heat-transfer liquids, especiallypreferably wood.

Microorganisms which may bring about degradation of, or change in, theindustrial materials, and which may be mentioned are, for example,bacteria, fungi, yeasts, algae and slime organisms. The active compoundsaccording to the invention preferably act against fungi, in particularmoulds, wood-discolouring and wood-destroying fungi (Basidiomycetes),and against slime organisms and algae.

Microorganisms of the following genera may be mentioned by way ofexample:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, microencapsulations in polymeric substances and in coatingcompositions for seed, and also ULV cold- and warm-fogging products.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents,pressurized liquified gases and/or solid carriers, optionally with theuse of surfactants, that is emulsifiers and/or dispersants and/orfoam-formers. If water is used as an extender, organic solvents can, forexample, also be used as cosolvents. Liquid solvents which are mainlysuitable are: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics and chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, mineral and vegetable oils, alcohols such as butanol orglycol as well as their ethers and esters, ketones such as acetone,methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, stronglypolar solvents such as dimethylformamide and dimethyl sulphoxide, andwater. Liquified gaseous extenders or carriers are those liquids whichare gaseous at normal temperature and under atmospheric pressure, forexample aerosol propellents such as halogenohydrocarbons and alsobutane, propane, nitrogen and carbon dioxide. Solid carriers which aresuitable are: for example, ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals such as highly disperse silica,alumina and silicates. Suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and synthetic granules of inorganic andorganic meals, and granules of organic material such as sawdust, coconutshells, maize cobs and tobacco stalks. Suitable emulsifiers and/or foamformers are: for example, non-ionic and anionic emulsifiers, such aspolyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers,for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates and protein hydrolysates. Suitabledispersants are: for example, lignin-sulphite waste liquors andmethylcellulose.

Adhesives such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices such as gum arabic,polyvinyl alcohol and polyvinyl acetate, and natural phospholipids suchas cephalins and lecithins, and synthetic phospholipids can be used inthe formulations. Further additives can be mineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention may be present, as suchor in their formulations, in a mixture with known fungicides,bactericides, acaridices, nematicides, or insecticides, for example towiden the spectrum of action or to prevent the build-up of resistance.In many cases, synergistic effects result, i.e. the activity of themixture exceeds the activity of the individual components.

Examples of suitable components in mixtures are the following compounds:

Fungicides

aldimorph, ampropylfos, ampropylfos-potassium, andoprim, anilazine,azaconazole, azoxystrobin,

benalaxyl, benodanil, benomyl, benzamacril, benzamacryl-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvone, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

debacarb, dichlorophen, diclobutrazole, diclofluanid, diclomezin,dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph,diniconazole, diniconazole-M, dinocap, diphenylamin, dipyrithione,ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

ediphenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan,fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentinhydroxyde, ferbam, ferimzone, fluazinam, flumetover, fluoromid,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

guazatine,

hexachlorobenzene, hexaconazole, hymexazol,

imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolan, isovaledione,

kasugamycin, kresoxim-methyl, copper preparations such as: copperhydroxide, copper naphthenate, copper oxychloride, copper sulphate,copper oxide, oxine-copper and Bordeaux mixture,

mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiornycin, myclobutanil, myclozolin,

nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim, oxyfenthiine,

paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole,prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole,propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, pyroxyfur,

quinconazole, quintozene (PCNB),

sulphur and sulphur preparations,

tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole,

uniconazole,

validamycin A, vinclozolin, viniconazole,

zarilamid, zineb, ziram and also

Dagger G,

OK-8705,

OK-8801,

-   α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,-   α-(2,4-dichlorophenyl)-β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,-   α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,    (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,    (E)-a-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,    1-isopropyl    {2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbonate-   1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanone    O-(phenylmethyl)-oxime,-   1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,-   1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,-   1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,-   1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,-   1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,-   1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,-   1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol,-   2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,-   2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide,-   2,6-dichloro-5-(methylthio)-4-pyrimidinyl thiocyanate,-   2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,-   2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,-   2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,-   2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole,-   2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-a-D-glucopyranosyl]-amino]4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,-   2-aminobutane,-   2-bromo-2-(brommethyl)-pentanedinitrile,-   2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,-   2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,-   2-phenylphenol(OPP),-   3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,-   3,5-dichloro-N-[cyano[(1-methyl-2-propynyl)-oxy]-methyl]-benzamide,-   3-(1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,-   3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,-   4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,-   4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,-   8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,-   8-hydroxyquinolin sulphate,    9H-xanthene-9-carboxylic acid 2-[(phenylamino)-carbonyl]-hydrazide,-   bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophene    dicarboxylate,-   cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,-   cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine    hydrochloride,    Ethyl [(4-chlorophenyl)-azo]-cyanoacetate,    potassium hydrogen carbonate,-   Sodium methane tetrathiolate,-   methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,-   methyl N-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,-   methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,-   N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,-   N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,-   N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,-   N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,-   N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,-   N-(6-methoxy)-3-pyridinyl)-cyclopropanecarboxamide,-   N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,-   N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,-   sodium N-formyl-N-hydroxy-DL-alaninate,-   O,O-diethyl    [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,-   O-methyl S-phenyl phenylpropylphosphoramidothioate,-   S-methyl 1,2,3-benzothiadiazole-7-carbothibate,-   spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,-   4-[3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-acryloyl]-morpholine.

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/Acaricides/Nematicides

abamectin, acephate, acetamiprid, acrinathrin, alanycarb, aldicarb,aldoxycarb, alphacypermethrin, alphamethrin, amitraz, avermectin, AZ60541, azadirachtin, azamethiphos, azinphos A, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillusthuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella,bendiocarb, benfuracarb, bensultap, benzoximate, betacyfluthrin,bifenazate, bifenthrin, bioethanomethrin, biopermethrin, bistrifluron,BPMC, bromophos A, bufencarb, buprofezin, butathiofos, butocarboxim,butylpyridaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron,diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,dimethylvinphos, diofenolan, disulfoton, docusate-sodium, dofenapyn,

eflusilanate, emamectin, empenthrin, endosulfan, Entomophthora spp.,esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox, etoxazole,etrimfos,

fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb,fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad, fenpyrithrin,fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron,flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate,fubfenprox, furathiocarb,

granulosis viruses

halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene,

imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,

nuclear polyhedrosis viruses

lambda-cyhalothrin, lufenuron

malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,mevinphos, milbemectin, milbemycin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron

ometboate, oxamyl, oxydemethon M

Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,propargite, propoxur, prothiofos, prothoate, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,pyriproxyfen,

quinalphos,

ribavirin

salithion, sebufos, silafluofen, spinosad, spirodiclofen, sulfotep,suiprofos,

tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimiphos,teflubenzuron, tefluthrin, temephos, temivinphos, terbufos,tetrachlorvinphos, tetradifon, theta-cypermethrin, thiacloprid,thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogen oxalate,thiodicarb, thiofanox, thuringiensin, tralocythrin, tralomethrin,triarathene, triazamate, triazophos, triazuron, trichlophenidine,trichlorfon, triflumuron, trimethacarb,

vamidothion, vaniliprole, Verticillium lecanii

YI 5302

zeta-cypermethrin, zolaprofos

(1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]2,2-dimethylcyclopropanecarboxylate

(3-phenoxyphenyl)-methyl 2,2,3,3-tetramethylcyclopropanecarboxylate

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazin-2(1H)-imine

-   2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole-   2-(acetlyoxy)-3-dodecyl-1,4-naphthalenedione,-   2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide-   2-chloro-N-[[[4-(2,2-dichloro-1,1-difluorethoxy)-phenyl]-amino]-carbonyl]-benzamide-   3-methylphenyl propylcarbamate-   4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene-   4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone-   4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone-   4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorphenyl)-3(2H)-pyridazinone    Bacillus thuringiensis strain: EG-2348-   [2-benzoyl-1-(1,1-dimethylethyl)]-benzohydrazide-   2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl-ester    butanoate-   [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide-   dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde-   ethyl    [2-[[1,6-dibydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate-   N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine-   N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide-   N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine-   N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazine dicarbothioamide-   N-methyl-N′-2-propenyl-1,2-hydrazine dicarbothioamide-   O,O-diethyl [2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate-   N-cyanomethyl-4-trifluoromethyl-nicotinamide-   3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethylpyridin-2-yloxy)-propoxy]-benzene

A mixture with other known active compounds such as herbicides or withfertilizers and growth regulators is also possible.

In addition, the compounds of the formula (I) according to the inventionalso exhibit very good antimycotic actions. They have a very broadantimycotic spectrum of action, in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata) and also Epidermophytonfloccosum, Aspergillus species such as Aspergillus niger and Aspergillusfumigatus, Trichophyton species such as Trichophyton mentagrophytes.

Microsporon species such as Microsporon canis and audouinii. Theelimination of these fungi constitutes in no way a limitation of themycotic spectrum which can be controlled, but has merely illustrativecharacter.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. They are applied in the customary fashion, for example bypouring, spraying, atomizing, spreading, dusting, foaming, brushing onand the like. It is furthermore possible to apply the active compoundsby the ultra-low-volume method or to inject the active compoundpreparation, or the active compound itself, into the soil. The seed ofthe plants may also be treated.

When employing the active compounds according to the invention asfungicides, the application rates can be varied within a substantialrange, depending on the type of application. When treating plant parts,the application rates of active compounds are generally between 0.1 and10 000 g/ha, preferably between 10 and 1000 g/ha. In the treatment ofseed, the application rates of active compound are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. In the treatment of the soil, the applicationrates of active compound are generally between 0.1 and 10 000 g/ha,preferably between 1 and 5 000 g/ha.

The preparation and the use of the active compounds according to theinvention can be seen from the examples which follow.

PREPARATION EXAMPLES Example I-1-a-1

13.8 g of the compound of Example (II-1) in 28 ml of absolute DMF areadded dropwise at 0–10° C. to 8.95 g (0.075 mol) of potassiumtert-butoxide in 23 ml of absolute dimethylformamide (DMF).

The mixture is stired at 20° C. until the reaction has ended (check bythin-layer chromatography (TLC)).

250 ml of ice-water are added, the mixture is acidified at 0–10° C. withconcentrated hydrochloric acid to pH 2 and filtered with suction. Thisis followed by washing with ice-water, drying and boiling up in methyltert-butyl ether (MTBE)/n-hexane.

This is followed by purification by column chromatography on silica gel(dichloromethane/acetone, 5:1).

Yield: 10.58 g (86% of theory)

The following compounds of the formula (I-1-a) are obtained analogouslyto Example (I-1-a-1) and following the general preparation instructions:

(I-1-a)

Ex. No. X Y A B D Q¹ Q² M.p. ° C. I-1-a-2 CH₃ 4-Cl—C₆H₄ H H —(CH₂)₄— H141 I-1-a-3 CH₃ 4-Cl—C₆H₄ —(CH₂)₂—O—(CH₂)₂— H H H I-1-a-4 CH₃ 4-Cl—C₆H₄H H H —(CH₂)₂—O—(CH₂)₂— 236 I-1-a-5 Cl 4-Cl—C₆H₄ H H H CH₃ CH₃ 183I-1-a-6 CH₃ 4-Cl—C₆H₄ H H

CH₃ CH₃ 165 I-1-a-7 CH₃ 4-CF₃—C₆H₄ H H H CH₃ CH₃ 181 I-1-a-8 CH₃3-Cl—C₆H₄ H H CH₃ CH₃ 173 I-1-a-9 CH₃ 2-Cl-4- H H H CH₃ CH₃ 212OC₂H₅—C₆H₃ I-1-a-10 CH₃ 4-CH₃—C₆H₄ H H H CH₃ CH₃ 209 I-1-a-11 C₂H₅4-Cl—C₆H₄ H H H CH₃ CH₃ 210 I-1-a-12 C₃H₇ 4-Cl—C₆H₄ H H H CH₃ CH₃ 215I-1-a-13 CH₃ 4-Cl—C₆H₄ CH₃ CH₃ H CH₃ CH₃ 254 I-1-a-14 Cl 4-Cl—C₆H₄ CH₃CH₃ H CH₃ CH₃

Example I-1-b-1

1.05 g of the compound of Ex. I-1-a-1 are introduced into 30 ml ofanhydrous ethyl acetate and treated with 0.46 ml (3.3 mmol) oftriethylamine. 0.34 ml (0.0033 mol) of isobutyrol chloride in 5 ml ofanhydrous ethyl acetate is added dropwise under reflux, and stirring iscontinued under reflux until the reaction has ended (check by thin-layerchromatography). The solvent is distilled off in vacuo and the residueis taken up in dichloromethane. This is washed 2× with 20 ml of 0.5 NNaOH solution and dried, and the solvent is evaporated.

This is followed by purification by column chromatography over silicagel (dichloromethane/ethyl acetate 3:1) Yield: 0.57 g (45% of theory),M.p.: 189° C.

The following compounds of the formula I-1-b are obtained analogously toExample I-1-b-1 and following the general preparation instructions:

(I-1-b)

Ex. No. X Y A B D Q¹ Q² R¹ M.p. ° C. I-1-b-2 CH₃ 4-Cl—C₆H₄ H H H CH₃ CH₃

229 I-1-b-3 CH₃ 4-Cl—C₆H₄ H H H CH₃ CH₃

213 I-1-b-4 CH₃ 4-Cl—C₆H₄ H H H CH₃ CH₃ C₂H₅O—CH₂— 168

Example I-1-c-1

0.1 ml (1 mmol) of ethyl chloroformate in 1 ml of absolutedichloromethane are added at 10–20° C. to 0.35 g of the compound ofExample (I-1-a-1) in 11 ml of absolute dichloromethane and 0.1 ml (1mmol) of triethylamine.

The mixture is stirred at room temperature until the reaction has ended(TLC check) and the solvent is evaporated on a rotary evaporator. Theprecipitate is taken up in dichloromethane and the mixture is washedtwice with 5 ml of 0.5 N sodium hydroxide solution, dried andconcentrated.

This is followed by purification by column chromatography on silica gel(dichloromethane/ethyl acetate 5:1).

Yield: 0.17 g (40% of theory)

The following compounds of the formula (I-1-c) are obtained analogouslyto Example (I-1-c-1) and following the general preparation instructions

(I-1-c)

Ex. No. X Y A B D Q¹ Q² M R² M.p. ° C. I-1-c-2 CH₃ 4-Cl—C₆H₄ H H H CH₃CH₃ O

210 I-1-c-3 CH₃ 4-Cl—C₆H₄ H H H CH₃ CH₃ O

209 I-1-c-4 CH₃ 4-Cl—C₆H₄ H H H CH₃ CH₃ S

198

Ex. No. I-1-g-1

1.05 g of the compound of Example I-1-a-1 are introduced into 10 ml ofanhydrous ethyl acetate, and 0.42 ml (3 mmol) of triethylamine wereadded. 0.4 ml (0.0033 mol) of morpholinocarbamoyl chloride in 2 ml ofanhydrous ethyl acetate are added dropwise under reflux, and stirring iscontinued under reflux until the reaction has ended (check by thin-layerchromatography). The solvent is distilled off and the residue is takenup in dichloromethane. The mixture is washed 2× with 20 ml of 0.5 N NaOHsolution and dried, and the solvent is evaporated.

This is followed by purification by column chromatography over silicagel (dichloromethane/ethyl acetate, 5:1) Yield: 0.22 g (15% of theory),M.p.: 217° C.

Example II-1

18 g of 5-methyl-2-(4-chloro-phenyl)-thiazolylacetic acid are added to10 g of ethyl 3-amino-3-methyl-butyrate in 250 ml of absolutetetrahydrofuran and 12 ml of triethylamine, and the mixture is stirredfor 15 minutes at room temperature. 13.2 ml of triethylamine aresubsequently added, and 3.4 ml of phosphorus oxychloride are immediatelyadded dropwise in such a way that the solution boils moderately.

The mixture is stirred for a further 30 minutes under reflux. Then, thereaction solution is stirred into 800 ml of ice-water and extracted withdichloromethane, and the dichloromethane phase is dried and evaporated.This is followed by purification by column chromatography on silica gel(n-hexane/ethyl acetate, 2:1).

Yield: 13.81 g (52% of theory), M.p. 101° C.

The following compounds of the formula (II) are obtained analogously toExample (II-1) and following the general preparation instructions:

(II)

Ex. No. X Y A B D Q¹ Q² R⁸ M.p. ° C. II-2 CH₃ 4-Cl—C₆H₄ H H —(CH₂)₄— HC₂H₅ oil II-3 CH₃ 4-Cl—C₆H₄ —(CH₂)₂—O—(CH₂)₂— H H H C₂H₅ 127  II-4 CH₃4-Cl—C₆H₄ H H H —(CH₂)₂—O—(CH₂)₂— C₂H₅ 129  II-5 Cl 4-Cl—C₆H₄ H H H CH₃CH₃ C₂H₅ 115  II-6 CH₃ 4-Cl—C₆H₄ H H

CH₃ CH₃ C₂H₅ 86 II-7 CH₃ 4-CF₃—C₆H₄ H H H CH₃ CH₃ C₂H₅ 94 II-8 CH₃3-Cl—C₆H₄ H H H CH₃ CH₃ C₂H₅ 89 II-9 CH₃ 2,4-Cl₂—C₆H₃ H H H CH₃ CH₃ C₂H₅93 II-10 CH₃ 4-CH₃—C₆H₄ H H H CH₃ CH₃ C₂H₅ 88 II-11 C₂H₅ 4-Cl—C₆H₄ H H HCH₃ CH₃ C₂H₅ 105  II-12 C₃H₇ 4-Cl—C₆H₄ H H H CH₃ CH₃ C₂H₅ 69 II-13 CH₃4-Cl—C₆H₄ CH₃ CH₃ H CH₃ CH₃ CH₃ 144  II-14 Cl 4-Cl—C₆H₄ CH₃ CH₃ H CH₃CH₃ CH₃ 87 II-15 Cl 4-Cl—C₆H₄ CH₃ CH₃ H H H C₂H₅ 99 II-16 C₂H₅ 4-Cl—C₆H₅H H H —(CH₂)₂—O—(CH₂)2)— C₂H₅ oil

Example I-2-a-1

1.5 g of the compound of Example III-1 in 5 ml of absolute acetonitrileare added at room temperature to 0.68 g (6 mmol) of potassiumtert-butoxide in 10 ml of absolute acetonitrile.

The mixture is stirred for 3 hours at room temperature. The solution ispoured into ice-water, acidified with 1 N hydrochloric acid, filteredoff with suction and dried. This is followed by purification by columnchromatography on silica gel (n-hexane/ethyl acetate 5:1).

Yield: 0.23 g (16% of theory) M.p. 138–140° C.

The following compounds of the formula (I-2-a) are obtained analogouslyto Example (I-2-a-1) and following the general preparation instructions:

(I-2-a)

Ex. No. X Y A B Q¹ Q² M.p. ° C. I-2-a-2 CH₃ 4-Cl—C₆H₄ CH₃ CH₃ H H 133I-2-a-3 C₂H₅ 4-Cl—C₆H₄ CH₃ CH₃ H H 129 I-2-a-4 C₂H₅ 4-Cl—C₆H₄ CH₃ CH₃CH₃ CH₃ 144–145

Example-No. I-2-b-1

190 mg of the compound of Example I-2-a-1 in 5 ml of anhydrousdichloromethane are treated with 0.105 ml of triethylamine. 115 mg of6-chloronicotinoyl chloride are added with ice-cooling, and the mixtureis stirred at room temperature.

The reaction solution is washed 1× with 10% citric acid solution, theaqueous phase is extracted with dichloromethane, the organic phase iswashed 1× with 1 N NaOH, and the aqueous phase is extracted withdichloromethane. This is followed by drying and evaporation of thesolvent on a rotary evaporator.

Yield: 0.17 g (65% of theory)

¹H NMR (DMSO, 400MHz): δ=1.30, 1.56 (2 s, in each case 6H, 4 CH₃) 2.29(s, 3H, thiazolyl-CH ₃), 7.41, 7.59 (2d, in each case 2H, Ar—H) 7.57 (d,1H, pyridyl-H), 8.25 (d, 1H, pyridyl-H), 8.83 (s, 1H, pyridyl-H) ppm.

The following compounds of the formula (I-2-b) are obtained analogouslyto Example (I-2-b-1) and following the general preparation instructions

(I-2-b)

Ex. No X Y A B Q¹ Q² R¹ M.p. ° C. I-2-b-2 CH₃ 4-Cl—C₆H₄ CH₃ CH₃ H Hi-C₄H₉ oil I-2-b-3 C₂H₅ 4-Cl—C₆H₄ CH₃ CH₃ H H H₅C₂—CH₂— oil

Example-No. 1–2-c-1

300 mg (0.8 mmol) of the compound of Example I-2-a-1 in 10 ml ofanhydrous dichloromethane are treated with 0.17 ml (1.2 mmol) oftriethylamine. 0.1 ml (1.04 mmol) of ethyl chloroformate is subsequentlyadded at 0° C.

The mixture is stirred at room temperature.

The reaction solution is washed 1× with 10% citric acid solution, theaqueous phase is extracted with dichlromethane, the organic phase iswashed 1× with 1 N NaOH, and the aqueous phase is extracted withdichloromethane. This is followed by drying and evaporation of thesolvent on a rotary evaporator.

Yield: 0.3 g (83% of theory).

¹H NMR (400 MHz, CDCl₃): δ=0.94 (t, 3H, CH ₃—CH₂—O), 1.22 (s, 6H, 2CH₃),1.48 (s, 6H, 2CH₃), 1.27 (s, 3H, CH₃), 3.95 (q, CH ₃—CH₂—O), 7.56 (d,2H, arom. CH), 7.83 (d, 2H, arom. CH) ppm.

The following compound of the formula (I-2-c) is obtained analogously toExample (I-2-c-1) and following the general preparation instructions

(I-2-c)

Ex. No. X Y A B Q¹ Q² M R² M.p. ° C. I-2-c-2 CH₃ 4-Cl—C₆H₄ CH₃ CH₃ H H OC₂H₅ oil I-2-c-3 C₂H₅ 4-Cl—C₆H₄ CH₃ CH₃ H H O C₂H₅ oil I-2-c-4 C₂H₅4-Cl—C₆H₄ CH₃ CH₃ H H S

oil

Example III-1

1.6 ml of triethylamine are added to 1.12 g (6.4 mmol) of ethyl3-hydroxy-2,2,3-trimethyl-butyrate in 20 ml of absolute tetrahydrofuran.The mixture is stirred for 5 minutes, and 1.07 g (4 mmol) of5-methyl-2-(4-chlorophenyl)-thiazolylacetic acid are added. After afurther 15 minutes, 0.9 ml of triethylamine is added, and 0.2 ml ofphosphorus oxychloride is immediately added in such a way that thesolution boils moderately. The mixture is stirred for 1 hour underreflux.

The mixture is concentrated and the product is purified by columnchromatography on silica gel (dichloromethane→dichloromethane:ethylacetate, 3:1).

Yield: 1.5 g (88% of theory)

¹H NMR (400 MHz, DMSO): δ=1.11, 1.12 (2 s, in each case 6H, 4–CH₃), 1.17(t, 3H, CH ₃—CH₂—O), 2.41 (s, CH ₃-thiazolyl), 7.52, 7.82 (2 d, in eachcase 2H, aryl-H) ppm.

The following compounds of the formula (III) are obtained analogously toExample (III-1) and following the general preparation instructions:

(III)

Ex. No. X Y A B Q¹ Q² R⁸ M.p. ° C. III-2 CH₃ 4-Cl—C₆H₄ CH₃ CH₃ H H CH₃Oil* III-3 C₂H₅ 4-Cl—C₆H₄ CH₃ CH₃ H H CH₃ Oil* III-4 C₂H₅ 4-Cl—C₆H₄ CH₃CH₃ CH₃ CH₃ C₂H₅ Oil* Spectroscopic data, Ex. III-4: ¹H NMR (400 MHz,DMSO): δ = 1.04, 1.10, 1.11, 1.50 (4 s, in each case 3 H, 4-CH₃), 1.20(m, 3H, CH ₃—CH₂—O), 4.02 (m, 2 H, CH₃—CH ₂—O) ppm. *The oils wereconverted into the corresponding compounds of the formula 1-2-a withoutbeing characterized further.

Use Examples Example A Meloidogyne Test

Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted to the desired concentrationwith water.

Containers are filled with sand, active compound solution, Meloidogyneincognita egg/larval suspension and lettuce seeds. The lettuce seedsgerminate and the plantlets develop. The galls develop on the roots.

After the desired time, the nematicidal efficacy is determined in % withreference to gall formation. 100% means that no galls were found; 0%means that the number of galls on the treated plants corresponds to thatof the untreated control.

In this test, a destruction rate of 100% is shown, for example, by thecompounds of Preparation Examples I-1-c-1 and I-2-a-1 at an activecompound concentration of 20 ppm, and a destruction rate of 98% after 14days by the compound of Preparation Example I-2-a-3 at an activecompound concentration of 20 ppm.

Example B Myzus Test

Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted to the desired concentrationwith emulsifier-containing water.

Cabbage leaves (Brassica oleracea) which are severely infested by thegreen peach aphid (Myzus persicae) are treated by immersing into theactive compound preparation of the desired concentration.

After the desired time, the destruction rate is determined in %. 100%means that all of the aphids have been destroyed; 0% means that none ofthe aphids have been destroyed.

In this test, a destruction rate of 90% was caused, after 6 days, by thecompound of Preparation Example I-2-a-1 at an active compoundconcentration of 500 ppm.

Example C Phaedon Larvae Test

Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted to the desired concentrationwith emulsifier-containing water.

Cabbage leaves (Brassica oleracea) are treated by immersing in theactive compound preparation of the desired concentration and populatedwith larvae of the mustard beetle (Phaedon cochleariae) while the leavesare still moist.

After the desired time, the destruction rate is determined in %. 100%means that all the beetle larvae have been destroyed; 0% means that noneof the beetle larvae have been destroyed.

In this test, a destruction rate of 100% is shown, after 7 days, forexample by the compounds of Preparation Examples I-1-a-1 and I-2-a-2 atan active compound concentration of 1000 ppm, and a destruction rate of100% after 7 days by the compound of Preparation Example I-2-a-1 at anactive compound concentration of 500 ppm.

Example D Plutella Test/Synthetic Feed

Solvent: 100 parts by weight of acetone Emulsifier: 1900 parts by weightof methanol

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted to the desired concentrationwith methanol.

A stated amount of active compound preparation of the desiredconcentration is pipetted onto a standardized amount of synthetic feed.After the methanol has evaporated, a film can lid populated with approx.100 Plutella eggs is placed into each cavity. The freshly hatched larvaemigrate onto the treated synthetic feed.

After the desired time, the destruction rate is determined in %. 100%means that all of the animals have been destroyed; 0% means that none ofthe animals have been destroyed.

In this test, a destruction rate of 100% is shown, after 7 days, forexample by the compound of Preparation Example I-2-a-4 at an activecompound concentration of 1000 ppm.

Example E Spodoptera frugiperda Test

Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted to the desired concentrationwith emulsifier-containing water.

Cabbage leaves (Brassica oleracea) are treated by immersing in theactive compound preparation of the desired concentration and populatedwith larvae of the fall armyworm caterpillars (Spodoptera frugiperda)while the leaves are still moist.

After the desired time, the destruction rate is determined in %. 100%means that all the caterpillars have been destroyed; 0% means that noneof the caterpillars have been destroyed.

In this test, a destruction rate of 100% is shown, after 7 days, forexample by the compounds of Preparation Examples I-2-a-2 at an activecompound concentration of 1000 ppm and I-2-a-1 at an active compoundconcentration of 500 ppm.

Example F Tetranychus Test (OP Resistant/Immersion Treatment)

Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part byweight of alkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amounts of solvent andemulsifier and the concentrate is diluted to the desired concentrationwith emulsifier-containing water.

Bean plants (Phaseolus vulgaris) which are severely infested by allstages of the two-spotted spider mite (Tetranychus urticae) are immersedinto an active compound preparation of the desired concentration.

After the desired time, the efficacy is determined in %. 100% means thatall of the spider mites have been destroyed; 0% means that none of thespider mites have been destroyed.

In this test, destruction rates of 100% (Example I-2-a-1), 99% (ExampleI-2-a-2), 98% (Example I-1-a-1) and 90% (Examples I-2-a-3 and I-2-a-4),respectively, are shown by the compounds of Preparation ExamplesI-1-a-1, I-2-a-2, I-2-a-3, I-2-a-1 and I-2-a-4 at an active compoundcomposition of 100 ppm.

Example G Post-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent, the statedamount of emulsifier is added, and the concentrate is diluted with waterto the desired concentration.

Test plants which have a height of 5 to 15 cm are sprayed with theactive compound preparation in such a way that the active compoundquantities desired in each case are applied per unit area. Theconcentration of the spray mixture is chosen such that the activecompound quantities desired in each case are applied in 1000 1 ofwater/ha.

After three weeks, the degree of damage to the plants is scored in %damage in comparison with the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

Example H Pre-emergence Test

Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent, the statedamount of emulsifier is added, and the concentrate is diluted with waterto the desired concentration.

Seeds of the test plants are sown in normal soil. After approximately 24hours, the soil is sprayed with the active compound preparation in sucha way that the active compound quantities desired in each case areapplied per unit area. The concentration of the spray mixture is chosensuch that the active compound quantities desired in each case areapplied in 1000 l of water/ha.

After three weeks, the degree of damage to the plants is scored in %damage in comparison with the development of the untreated control.

The figures denote:

-   -   0%=no effect (like untreated control)    -   100%=total destruction

pre- g Sugar emergence ai/ga beet Digitaria Lolium Setaria MatricariaEx. 125 0 100  100 100  95 I-2-a-1 post- g Sugar Avena emergence ai/haWheat beet Alopecurus fatua Digitaria Setaria Ex. 125 10   0  90  90  95100 I-2-a-1 pre- g Sugar Avena emergence ai/ha beet fatua Lolium SetariaMatricaria Solanum Ex. 125 0 95 100 100 100  95 I-2-a-4 post- g SugarAvena emergence ai/ha beet fatua Digitaria Lolium Setaria Ex. 125 0 95100 100 100 I-2-a-4

Example I Limit Concentration Test/Soil-dwelling Insects—Treatment ofTransgenic Plants

Test insect: Diabrotica balteata larvae in the soil Solvent: 7 parts byweight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycolether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent, the statedamount of emulsifier is added, and the concentrate is diluted with waterto the desired concentration.

The active compound preparation is poured onto the soil. Theconcentration of the active compound in the preparation is of virtuallyno importance, only the weight of active substance per unit volume ofsoil, which is indicated in ppm (mg/l), being decisive. The soil isfilled into 0.25 l pots, and these are left to stand at 20° C.

Immediately after the test is set up, 5 pregerminated maize kernels cv.YIELD GUARD (trademark of Monsanto Comp., USA) are placed into each pot.The appropriate test insects are put in to the heated soil after 2 days.After a further 7 days, the efficacy of the active compound isdetermined by counting the maize plants which have emerged (1 plant=20%action).

Example J Heliothis Virescens Test—Treatment of Transgenic Plants

Solvent: 7 parts by weight of acetone Emulsifier: 1 part by weight ofalkylaryl polyglycol ether

To prepare a suitable active compound preparation, 1 part by weight ofactive compound is mixed with the stated amount of solvent, the statedamount of emulsifier is added, and the concentrate is diluted with waterto the desired concentration.

Sojabean shoots (Glycine max) cv. Roundup Ready (trademark of MonsantoComp. USA) are treated by immersing into the active compound preparationof the desired concentration and populated with the tobacco budwormHeliothis virescens while the leaves are still moist.

The destruction of the insects is determined after the desired time.

1. Compounds of the formula (I)

in which Het represents

W represents oxygen X represents hydrogen or C₁–C₆-alkyl, Y representshalogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy,C₁–C₆-halogenoalkoxy, or a group

in which V¹ represents hydrogen, halogen, C₁–C₁₂-alkyl,C₁–C₆-alkoxy,_C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl,C₁–C₆-alkylsulphonyl, C₁–C₄-halogeno-alkyl, C₁–C₄-halogenoalkoxy, nitro,cyano, or represents phenyl, phenoxy, phenoxy-C₁–C₄-alkyl,phenyl-C₁–C₄-alkoxy, phenylthio-C₁–C₄-alkyl, or phenyl-C₁–C₄-alkylthio,each of which is optionally monosubstituted or polysubstituted byhalogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl,C₁–C₄-halogenoalkoxy, nitro, or cyano, and V² and V³ independently ofone another represent hydrogen, halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy,C₁–C₄-halogenoalkyl, or C₁–C₄-halogenoalkoxy, or V¹ and V² together withthe carbon atoms to which they are bonded represent a 5- or 6-memberedcycle that is optionally substituted by C₁–C₄-alkyl or halogen and inwhich one to three carbon atoms is optionally replaced by oxygen,sulphur, or nitrogen, A represents hydrogen; optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, oralkylthioalkyl; optionally substituted saturated or unsaturatedcycloalkyl in which one or more ring atoms is optionally replaced by ahetero atom; or aryl, arylalkyl or hetaryl, each of which is optionallysubstituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy,cyano, or nitro, B represents hydrogen or alkyl, or A and B togetherwith the carbon atom to which they are bonded represent a saturated orunsaturated, unsubstituted or substituted cycle that optionally containsat least one hetero atom; Q¹ represents hydrogen; alkyl; alkoxyalkyl;optionally substituted cycloalkyl in which one methylene group isoptionally replaced by oxygen or sulphur; or optionally substitutedphenyl, Q² represents hydrogen or alkyl, or Q¹ and Q² together with thecarbon atom to which they are bonded represent an unsubstituted orsubstituted cycle that optionally contains one hetero atom, and Grepresents hydrogen (a) or one of the groups

in which L represents oxygen or sulphur, M represents oxygen or sulphur,R¹ represents optionally halogen-substituted alkyl, alkenyl,alkoxyalkyl, alkylthioalkyl, or polyalkoxyalkyl; cycloalkyl that isoptionally substituted by halogen, alkyl, or alkoxy and that isoptionally interrupted by one or more hetero atoms; or optionallysubstituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl, orhetaryloxyalkyl, and R² represents optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, or polyalkoxyalkyl; or optionally substitutedcycloalkyl, phenyl, or benzyl.
 2. A Compound of formula (I) according toclaim 1 in which Het represents

W represents oxygen, X represents hydrogen or C₁–C₆-alkyl, Y representshalogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy,C₁–C₆-halogenoalkoxy, or a group

in which V¹ represents hydrogen, halogen, C₁–C₁₂-alkyl, C₁–C₆-alkoxy,C₁–C₆-alkylthio, C₁–C₆-alkylsulphinyl, C₁–C₆-alkylsulphonyl,C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, nitro, cyano, or representsphenyl, phenoxy, phenoxy-C₁–C₄-alkyl, phenyl-C₁–C₄-alkoxy,phenylthio-C₁–C₄-alkyl or phenyl-C₁–C₄-alkylthio, each of which isoptionally monosubstituted or polysubstituted by halogen, C₁–C₆-alkyl,C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl, C₁–C₄-halogenoalkoxy, nitro, orcyano, and V² and V³ independently of one another represent hydrogen,halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, C₁–C₄-halogenoalkyl, orC₁–C₄-halogenoalkoxy, or V¹ and V² together with the carbon atoms towhich they are bonded represent a 5- or 6-membered cycle which isoptionally substituted by C₁–C₄-alkyl or halogen and in which one tothree carbon atoms is optionally replaced by oxygen, sulphur ornitrogen, A represents hydrogen; C₁–C₁₂-alkyl, C₃–C₈-alkenyl, orC₁–C₆-alkoxy-C₁–C₄-alkyl, each of which is optionally substituted byhalogen; optionally halogen-, C₁–C₄-alkyl-, or C₁–C₄-alkoxy-substitutedC₃–C₈-cycloalkyl, or C₃–C₆-cyclo-alkyl-C₁–C₄-alkyl in which one or tworing members that are not directly adjacent are optionally replaced byoxygen and/or sulphur; or phenyl, benzyl, hetaryl having 5 to 6 ringatoms, or hetaryl-C₁–C₄-alkyl having 5 to 6 ring atoms each of whichphenyl, benzyl, hetaryl, or hetaryl-C₁–C₄-alkyl group is optionallysubstituted by halogen, C₁–C₆-alkyl, C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy,C₁–C₆-halogenoalkoxy, cyano, or nitro, B represents hydrogen orC₁–C₆-alkyl, or A, B, and the carbon atom to which they are bondedrepresent saturated C₃–C₁₀-cycloalkyl or unsaturated C₅–C₁₀-cycloalkylin which one ring member is optionally replaced by oxygen or sulphur andthat are optionally mono-substituted or disubstituted by C₁–C₆-alkyl,C₃–C₈-cycloalkyl, C₁–C₆-halogenoalkyl, C₁–C₆-alkoxy, C₁–C₆-alkylthio,halogen, or phenyl, Q¹ represents hydrogen; C₁ –C₆-alkyl;C₁–C₆-alkoxy-C₁–C₂-alkyl; C₃–C₈-cycloalkyl in which one methylene groupis optionally replaced by oxygen or sulphur and that is optionallysubstituted by fluorine, chlorine, C₁–C₄-alkyl, C₁–C₂-halogenoalkyl, orC₁–C₄-alkoxy; or phenyl that is optionally substituted by halogen,C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl, C₁–C₂-halogeno-alkoxy,cyano, or nitro, Q² represents hydrogen or C₁–C₄-alkyl, or Q¹ and Q²together with the carbon atom to which they are bonded representC₃–C₇-cycloalkyl in which one ring member is optionally replaced byoxygen or sulphur and that is optionally substituted by C₁–C₆-alkyl,C₁–C₆-alkoxy, or C₁–C₂-halogenoalkyl, and G represents hydrogen (a) orone of the groups

in which L represents oxygen or sulphur, M represents oxygen or sulphur,R¹ represents C₁–C₂₀-alkyl, C₁–C₂₀-alkenyl, C₁–C₈-alkoxy-C₁–C₈-alkyl,C₁–C₈-alkylthio-C₁–C₈-alkyl, or poly-C₁–C₈-alkoxy-C₁–C₈-alkyl, each ofwhich is optionally substituted by halogen; C₃–C₈-cycloalkyl in whichone or more ring members that are not directly adjacent are optionallyreplaced by oxygen and/or sulphur and that is optionally substituted byhalogen, C₁–C₆-alkyl, or C₁–C₆-alkoxy; phenyl that is optionallysubstituted by halogen, cyano, nitro, C₁–C₆-alkyl, C₁–C₆-alkoxy,C₁–C₆-halogenoalkyl, C₁–C₆-halogenoalkoxy, C₁–C₆-alkylthio, orC₁–C₆-alkylsulphonyl; phenyl-C₁–C₆-alkyl that is optionally substitutedby halogen, nitro, cyano, C₁C₆-alkyl, C₁–C₆-alkoxy,C₁–C₆-halogeno-alkyl, or C₁–C₆-halogenoalkoxy; 5- or 6-membered hetarylthat is optionally substituted by halogen, C₁–C₆-alkyl, ortrifluoromethyl; phenoxy-C₁–C₆-alkyl that is optionally substituted byhalogen or C₁–C₆-alkyl; or 5- or 6-membered hetaryloxy-C₁–C₆-alkyl thatis optionally substituted by halogen, amino, or C₁–C₆-alkyl, and R²represents C₁–C₂₀-alkyl, C₂–C₂₀-alkenyl, C₁–C₈-alkoxy-C₂–C₈-alkyl, orpoly-C₁–C₈-alkoxy-C₂–C₈-alkyl, each of which is optionally substitutedby halogen; C₃–C₈-cycloalkyl that is optionally substituted by halogen,C₁–C₆-alkyl, or C₁–C₆-alkoxy; or phenyl or benzyl, each of which isoptionally substituted by halogen, cyano, nitro, C₁–C₆-alkyl,C₁–C₆-alkoxy, C₁–C₆-halogenoalkyl, or C₁–C₆-halogenalkoxy.
 3. A compoundof formula (I) according to claim 1 in which

Het represents W represents oxygen, X represents hydrogen orC₁–C₄-alkyl; Y represents chlorine, bromine, C₁–C₄-alkyl,C₁–C₄-halogenoalkyl, C₁–C₄-alkoxy, C₁–C₄-halogenoalkoxy, or a group

in which V¹ represents hydrogen, fluorine, chlorine, bromine,C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl, C₁–C₂-halogenalkoxy,nitro, or cyano; or phenyl, phenoxy, phenoxy-₁–C₂-alkyl,phenyl-C₁–C₂-alkoxy, phenyl-thio-C₁–C₂-alkyl, or phenyl-C₁–C₂-alkylthio,each of which is optionally monosubstituted or disubstituted byfluorine, chlorine, bromine, C₁–C₄-alkyl, C₁–C₄-alkoxy,C₁–C₂-halogenoalkyl, C₁–C₂-halogenoalkoxy, nitro, or cyano, and V²represents hydrogen, fluorine, chlorine, bromine, C₁–C₄-alkyl,C₁–C₄-alkoxy, C₁–C₂-halogenoalkyl, or C₁–C₂-halogenoalkoxy, or V¹ and V²together with the carbon atoms to which they are bonded represent a 5-or 6-membered cycle in which one or two carbon atoms is optionallyreplaced by oxygen and that is optionally substituted by fluorine ormethyl, A represents hydrogen; C₁–C₈-alkyl or C₁–C₄-alkoxy-₁–C₂-alkyl,each of which is optionally substituted by fluorine; C₅–C₆-cycloalkyl orC₃–C₆-cycloalkyl-C₁–C₂-alkyl in which one ring member is optionallyreplaced by oxygen or sulphur and that is optionally substituted byfluorine, chlorine, methyl, ethyl, or methoxy; or phenyl or benzyl, eachof which is optionally substituted by fluorine, chlorine, bromine,C₁–C₄-alkyl, C₁–C₂-halogenoalkyl, C₁–C₄-alkoxy, or C₁–C₂-halogenoalkoxy,B represents hydrogen or C₁–C₄-alkyl, or A, B, and the carbon atom towhich they are bonded represent saturated C₅–C₇-cycloalkyl in which onering member is optionally replaced by oxygen and that is optionallymonosubstituted by C₁–C₄-alkyl, trifluoromethyl, or C₁–C₄-alkoxy, Q¹represents hydrogen, C₁–C₄-alkyl, or C₁–C₄-alkoxy-C₁–C₂-alkyl; orC₃–C₆-cycloalkyl in which one methylene group is optionally replaced byoxygen and that is optionally substituted by methyl or methoxy, Q²represents hydrogen, methyl, or ethyl, or Q¹ and Q² together with thecarbon atom to which they are bonded represent saturatedC₅–C₆-cycloalkyl in which one ring member is optionally replaced byoxygen and that is optionally substituted by C₁–C₄-alkyl orC₁–C₄-alkoxy, and G represents hydrogen (a) or one of the groups

in which L represents oxygen or sulphur, M represents oxygen or sulphur,R¹ represents C₁–C₁₆-alkyl, C₂–C₁₆-alkenyl, C₁–C₄-alkoxy-C₁–C₂-alkyl, orC₁–C₄-alkylthio-C₁–C₂-alkyl, each of which is optionally substituted byfluorine or chlorine; C₃–C₇-cycloalkyl in which one or two ring membersthat are not directly adjacent are optionally replaced by oxygen and/orsulphur and that is optionally substituted by fluorine, chlorine,C₁–C₅-alkyl or C₁–C₅-alkoxy; phenyl that is optionally substituted byfluorine, chlorine, bromine, cyano, nitro, C₁–C₄-alkyl, C₁–C₄-alkoxy,trifluoromethyl, or trifluoromethoxy; or pyridyl or thienyl, each ofwhich is optionally substituted by fluorine, chlorine, bromine, methyl,ethyl, or trifluoromethyl, and R² represents C₁–C₁₆-alkyl,C₂–C₁₆-alkenyl, or C₁–C₄-alkoxy-C₂–C₄-alkyl, each of which is optionallysubstituted by fluorine; C₃–C₇-cyclo-alkyl that is optionallysubstituted by methyl, ethyl or methoxy; or phenyl or benzyl, each ofwhich is optionally substituted by fluorine, chlorine, bromine, cyano,nitro, C₁–C₄-alkyl, C₁–C₃-alkoxy, trifluoro-methyl, or trifluoromethoxy.4. A compound of formula (I) according to claim 1 in which Hetrepresents

W represents oxygen, X represents methyl, ethyl, n-propyl, isopropyl,n-butyl, or isobutyl, Y represents methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, tert-butyl, or the group

in which V¹ represents hydrogen, fluorine, chlorine, bromine, methyl,ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, methoxy,ethoxy, n-propoxy, isopropoxy, trifluoromethyl, or trifluoromethoxy, andV² represents hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl,isopropyl, methoxy, ethoxy, trifluoromethyl, or trifluoromethoxy, Arepresents hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl,methoxymethyl, or ethoxymethyl, B represents hydrogen, methyl, or ethyl,or A, B, and the carbon atom to which they are bonded representsaturated C₅–C₆-cycloalkyl in which one ring member is optionallyreplaced by oxygen and that is optionally monosubstituted by methyl,ethyl, n-propyl, isopropyl, butyl, trifluoromethyl, methoxy, ethoxy,n-propoxy, or n-butoxy, Q¹ represents hydrogen, methyl, ethyl, propyl,isopropyl, cyclopropyl, cyclopentyl, or cyclohexyl, Q² representshydrogen, methyl, or ethyl, or Q¹ and Q² jointly with the carbon towhich they are bonded represent saturated C₅–C₆-cycloalkyl in which onering member is optionally replaced by oxygen and that is optionallysubstituted by methyl, ethyl, propyl, isopropyl, methoxy, ethoxy,propoxy, or butoxy, G represents hydrogen (a) or one of the groups

in which L represents oxygen or sulphur, M represents oxygen or sulphur,R¹ represents C₁–C₁-alkyl, C₂–C₁₄-alkenyl, C₁–C₄-alkoxy-C₁–C₂-alkyl, orC₁–C₄-alkylthio-C₁–C₂-alkyl, each of which is optionally substituted byfluorine or chlorine; C₃–C₆-cycloalkyl in which one or two ring membersthat are not directly adjacent are optionally replaced by oxygen and/orsulphur and that is optionally substituted by fluorine, chlorine,methyl, ethyl, or methoxy; phenyl that is optionally substituted byfluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl,tert-butyl, methoxy, trifluoromethyl, or trifluoromethoxy; or thienyl orpyridyl, each of which is optionally substituted by fluorine, chlorine,bromine, or methyl, and R² represents C₁–C₁₄-alkyl, C₂–C₁₄-alkenyl, orC₂–C₄-alkoxy-C₂–C₃-alkyl, each of which is optionally substituted byfluorine; C₃–C₆-cycloalkyl that is optionally substituted by methyl,ethyl, or methoxy; or phenyl or benzyl, each of which is optionallysubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl,isopropyl, tert-butyl, methoxy, trifluoromethyl, or trifluoromethoxy. 5.A compound of formula (I) according to claim 1 in which Het represents

W represents oxygen, X represents methyl, ethyl, n-propyl, or i-propyl,Y represents

A represents hydrogen or methyl, B represents hydrogen or methyl, or A,B, and the carbon atom to which they are bonded represent saturatedC₆-cycloalkyl in which one ring member is optionally replaced by oxygen,Q¹ represents hydrogen or methyl, Q² represents hydrogen or methyl, orQ¹ and Q² jointly with the carbon to which they are bonded representsaturated C₆-cycloalkyl in which one ring member is optionally replacedby oxygen, G represents hydrogen (a) or one of the groups

in which M represents oxygen or sulphur, R¹ represents C₁–C₄-alkyl, orC₁–C₄-alkoxy-C₁–C₂-alkyl; or phenyl or pyridyl, each of which isoptionally substituted by chlorine, and R² represents C₁–C₄-alkyl,phenyl, or benzyl.
 6. A process for the preparation of a compound offormula (I) according to claim 1 comprising (A) for substituted5,6-dihydropyrones of formula (I-2-a)

 in which A, B, Q¹, Q², and Het have the meanings given for formula (I),subjecting to an intramolecular condensation reaction an O-acylhydroxycarboxylic ester of formula (III)

in which A, B, Q¹, Q², and Het have the meanings given for formula (I),and R⁸ represents alkyl, in the presence of a diluent and in thepresence of a base, (B) for compounds of formula (I-2-b)

 in which A, B, Q¹, Q², R¹, and Het have the meanings given for formula(I), reacting a compound of the formulas (I-2-a) with (α) an acid halideof formula (IV)

 in which  R¹ has the meanings given for formula (I), and  Halrepresents halogen, or (β) a carboxylic anhydride of the formula (V)R¹—CO—O—CO—R¹  (V)  in which R¹ has the meanings given for formula (I),optionally in the presence of a diluent and optionally in the presenceof an acid binder; (C) for-compounds of formula (I-2-c)

 in which  A, B, Q¹, Q², R², M, and Het have the meanings given forformula (I), and  L represents oxygen, reacting a compound of theformulas (I-2-a) with a chloroformic ester or a chloroformic thioesterof formula (VI)R²-M-CO—Cl  (VI)  in which R² and M have the meanings given for formula(I), optionally in the presence of a diluent and optionally in thepresence of an acid binder; or (D) for compounds of formulas (I-2-c)

 in which  A, B, Q¹, Q², R², M, and Het have the meanings given forformula (I), and  L represents sulphur, reacting a compound of theformulas (I-2-a) with a chloromonothioformic ester or achlorodithioformic ester of formula (VII)

 in which R² and M have the meanings given for formula (I), optionallyin the presence of a diluent and optionally in the presence of an acidbinder.
 7. A pesticide, microbicide, or herbicide comprising aneffective amount of a compound of formula (I) according to claim 1 andone or more extenders and/or surfactants.
 8. A method of controllinganimal pests comprising allowing an effective amount of a compound offormula (I) according to claim 1 to act on the pests and/or theirenvironment.
 9. A method of controlling undesired vegetation comprisingallowing an effective amount of a compound of formula (I) according toclaim 1 to act on the undesired vegetation and/or its environment.
 10. Amethod of controlling fungi comprising allowing an effective amount of acompound of formula (I) according to claim 1 to act on the fungi and/ortheir environment.
 11. A process for the preparation of a pesticide,microbicide, or herbicide comprising mixing a compound of formula (I)according to claim 1 with one or more extenders and/or surfactants.